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Here is a chemical reaction formula: Reactants are:m3:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m6_m2:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O;m1_m6_m2:[Mg+2].[Br-].[Br-];m5:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4:COC(C)(C)C, Reagents are:m1_m6_m2:C1(=CC=CC=C1)C, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) in anhydrous toluene (15 mL) under an atmosphere of argon is treated with MgBr2 (3.5 g, 19.0 mol). The mixture is cooled to -25° C. and treated with lithium aluminum hydride (178 mg, 4.69 mmol) in one portion, followed by addition of anhydrous tert-butyl methyl ether (3.0 mL). The reaction is stirred at -20° C. for 2 hours and then overnight at room temperature. Additional lithium aluminum hydride (178 mg, 4.69 mmol) is added at room temperature and the reaction is stirred for 2 hours. The reaction is then quenched by slow addition of 1N NaOH (5 mL) followed by filtration through diatomaceous earth. The filtrate is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.3 g); cis/trans/1-2 +1-4 addition, 90/3/7. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:OC1C=CC(C1)=O;m1_m4_m2_m3:O1CCCC=C1;m1_m4_m2_m3:C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1, Reagents are:m1_m4_m2_m3:O1CCCC1;m5:C(C)(=O)OCC, and Products are 0:O1C(CCCC1)OC1C=CC(C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-hydroxy-2-cyclopentenone (1.41 g, 14.4 mmol) in tetrahydrofuran (24 mL) is treated with 3,4-dihydro-2H-pyran (2 mL) and pyridinium p-toluenesulfonate (500 mg, PPTS). The reaction is stirred at room temperature for 18 hours. The reaction mixture is then diluted with ethyl acetate (25 mL) and washed with 50% saturated brine (2×30 mL). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The resulting crude brown oil is purified by filtration through a plug of silica gel (25 g, 33% ethyl acetate/hexane) to provide the title compound as a yellow oil (2.00 g, 76%); 1H NMR (CDCl3) δ7.46 (2×dd, 1H, J=16.3, 5.7 Hz), 6.2 (m, 1H), 4.9 (m, 1H), 4.80 (d appt, 1H, J=23.8, 2.9 Hz), 3.9 (m, 1H), 3.6 (m, 1H), 2.73 (2×dd, 1H, J=18.4, 6.2 Hz), 2.35 (2×d, 1H, J=18.4 Hz), 1.8 (m, 1H), 1.6 (m, 4H); IR (neat) νmax 2944, 2870, 2855, 1723, 1348, 1202, 1182, 1152, 1128, 1078, 1032 cm-1 ; MS (CI) m/e (% relative intensity) 183 (M+H+, 28), 85(100). |
Here is a chemical reaction formula: Reactants are:m3_m5_m6:O1C(CCCC1)OC1C=CC(C1)=O;m4:[OH-].[Na+];m1_m2_m8_m7:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m2_m8_m7:[I-].[Li+], Reagents are:m3_m5_m6:COC(C)(C)C;m3_m5_m6:C1(=CC=CC=C1)C;m1_m2_m8_m7:C1(=CC=CC=C1)C;m1_m2_m8_m7:COC(C)(C)C, and Products are 0:O1C(CCCC1)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of lithium aluminum hydride (222 mg, 5.8 mmol), lithium iodide (3.2 g, 24 mmol), tert-butyl methyl ether (6 mL) and toluene (16 mL) is cooled to -15° C. A solution of 4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enone (2.179 g, 11.97 mmol, prepared in example 5) in tert-butyl methyl ether (2 mL) and toluene (2 mL) is added dropwise over 40 minutes. The reaction mixture is allowed to stir for 30 minutes. Then sodium hydroxide (1N, 5 mL) is added slowly to the reaction mixture. The slurry is filtered and the resulting phases separated. The aqueous phase is extracted with ethyl acetate (2×10 mL). The organic extracts are combined with the organic phase, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude oil is then purified by chromatography (silica gel, 30 g, 50% ethyl acetate/hexane, 400 mL) to provide the title compound (1.62 g, 73%), cis/trans/1-2+1-4 addition, 88/8/4; 1H NMR (CDCl3) δ6.1 (m, 1H), 4.7 (m, 1H), 4.6 (m, 2H), 3.9 (m, 1H), 3.5 (m, 1H), 2.7 (m, 1H), 1.4-2.0 (m, 8H); 13C NMR (CDCl3) δ 137.2,137.1, 134.8, 133.6, 98.3, 97.8, 79.7, 79.5, 74.7, 74.5, 62.6, 62.5, 42.0, 41.1, 31.1, 30.9, 25.4, 19.6, 19.5; IR (neat) νmax 2944, 2870, 2855, 1723, 1348, 1202, 1182, 1152, 1128, 1078, 1032 cm-1 ; MS (CI) m/e (% relative intensity) 183 (M+H+, 7), 167 (M+H+ -H2O, 40), 85(100). |
Here is a chemical reaction formula: Reactants are:m1_m5:OC1C=CC(C1)=O;m2_m3:ClC(C(OC(C)(C)C)=N)(Cl)Cl;m2_m3:B(F)(F)F.CCOCC;m4:C([O-])(O)=O.[Na+], Reagents are:m1_m5:C(Cl)Cl, and Products are 0:C(C)(C)(C)OC1C=CC(C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-hydroxy-2-cyclopentenone (1.15 g, 11.7 mmol) in methylene chloride is cooled to 3° C. and treated sequentially with tert-butyl trichloroacetimidate (4.2 mL, 23.7 mmol) and boron trifluoride diethyl etherate (0.15 mL). The reaction mixture is stirred at 3-10° C. for 2 hours and then allowed to warm to room temperature and stirred for 22 hours. The reaction mixture is then treated with sodium bicarbonate (250 mg) and filtered. The filtrate is concentrated under vacuum and the residue is purified by chromatography (silica gel, 39 g, 20% ethyl acetate/hexane, 600 mL) to provide the title compound (355 mg, 40%) as a yellow oil; 1H NMR (CDCl3)δ7.44 (dd, 1H, J=18 Hz), 6.2 (d, 1H, J=5.4 Hz), 4.8 (m, 1H), 2.68 (dd, 1H, J=5.8, 18 Hz), 2.25 (d, 1H, J=18 Hz), 1.27 (s, 9H); IR (neat) νmax 2976, 2936, 1721, 1368, 1352, 1188, 1103, 1161 cm-1 ; MS (CI) m/e (% relative intensity) 155 (M+H+, 22), 99 (100). |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)(C)OC1C=CC(C1)=O;m4:[OH-].[Na+];m1_m2_m6_m5:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m2_m6_m5:[I-].[Li+], Reagents are:m1_m2_m6_m5:C1(=CC=CC=C1)C;m1_m2_m6_m5:COC(C)(C)C, and Products are 0:C(C)(C)(C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of lithium aluminum hydride (55 mg, 1.44 mmol), lithium iodide (1.65 g, 5.76 mmol), tert-butyl methyl ether (2 mL) and toluene (3 mL) is cooled to -15° C. The slurry is treated dropwise with 4-tert-butoxy-cyclopent-2-enone(430 mg, 2.79 mmol, dissolved in 1 mL of toluene) over 5 minutes. The reaction mixture is stirred at -20° C. to -12° C. for 2 hours and then allowed to warm to room temperature and is stirred for 30 minutes. The reaction mixture is then treated sequentially with sodium hydroxide (1N, 1 mL), then tert-butyl methyl ether (10 mL) and filtered. The phases of the filtrate are separated and the aqueous phase is extracted with tert-butyl methyl ether (15 mL). The organic extracts and organic phase is combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by chromatography (silica gel, 30 g, 33% ethyl acetate/hexane) to provide the title compound (183 mg, 42%) as a yellow oil, cis/trans/1-2+1-4 addition, 87/9.8/3.2; 1H NMR (CDCl3) 6 5.9 (m, 1H), 5.8 (m, 1H), 4.6 (m, 1H), 4.5 (m, 1H), 2.7 (m, 1H), 2.0 (d,1H, J=9.6 Hz), 1.5 (d appt, 1H, J=4.5, 14 Hz), 1.2 (s, 9H); 13C NMR (CDCl3) δ136.6, 36, 75.5, 74.4, 74, 44.6, 28.7; νmax 3395, 2974, 2938, 907, 2878, 1389, 1364, 1117, 1169, 1022 cm-1 ; MS (CI) m/e (% relative intensity) 157 (M+H+ -H2O), 57, 83 (100). |
Here is a chemical reaction formula: Reactants are:m0_m4_m5_m6:C(Cl)(Cl)Cl;m0_m4_m5_m6:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O;m0_m4_m5_m6:C(Cl)(Cl)Cl;m1_m7:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O;m2_m3:C(C)N(CC)CC;m2_m3:C(C)(=O)OC=C, Reagents are:m1_m7:COC(C)(C)C, and Products are 0:[Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (10.0 g, 46.6 mmol, prepared in example 3a) is dissolved in tert-butyl methyl ether (60 mL, anhydrous). To the solution is added triethylamine (4.5 mL, 32.3 mmol), pancreatin (30 g, available from Sigma Chemical Company), and vinyl acetate (22 mL, 239 mmol). The reaction is allowed to stir for 7 hours at room temperature. The reaction is then filtered through diatomaceous earth and the filtrate is concentrated under vacuum. The products are separated by chromatography on silica gel (5% to 20% ethyl acetate/hexane) to provide (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (B, 6.1 g, 51% yield, 99% ee), [α]D -0.2°, (c=0.52, chloroform) as a yellow oil and (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (A, 4.7 g, 47% yield, >99% ee), [α]D -18.6°, (c=1.01, chloroform) as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m0_m4_m5_m6:C(Cl)(Cl)Cl;m0_m4_m5_m6:O1C(CCCC1)O[C@H]1C=C[C@H](C1)O;m0_m4_m5_m6:C(Cl)(Cl)Cl;m1_m7:O1C(CCCC1)O[C@H]1C=C[C@H](C1)O;m2_m3:C(C)N(CC)CC;m2_m3:C(C)(=O)OC=C, Reagents are:m1_m7:COC(C)(C)C, and Products are 0:O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (1.091 g, 5.92 mmol, prepared in example 6) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.59 mL, 4.2 mmol), pancreatin (3.2 g, available from Sigma Chemical Company), and vinyl acetate (2.7 mL, 29 mmol). The reaction is allowed to stir for 7 hours at room temperature. The reaction is then filtered through diatomaceous earth and the filtrate is concentrated under vacuum. The products are separated by chromatography on silica gel (10% to 20% ethyl acetate/hexane) to provide (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (B, 601 mg, 45% yield, 91% ee) [α]D =-19.8°,(c=1.00, chloroform) as a yellow oil and (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (A, 560 mg, 50% yield, 94% ee), [α]D =-9.9°, (c=1.06, chloroform) as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:O.[OH-].[Li+];m1_m4:[Si](C)(C)(C(C)(C)C)OC1C=CC(C1)OC(C)=O;m3:O, Reagents are:m1_m4:C1CCOC1.CO.O, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (2.3 mmol, prepared in example 10) in THF/methanol/water (2.7/0.9/0.9 mL). Add lithium hydroxide monohydrate (2.5 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound (452 mg, 92% yield) [α]20D =+21.8°, (c=1.02, chloroform). |
Here is a chemical reaction formula: Reactants are:m3_m4:COC(C)(C)C;m3_m4:O;m1_m5:O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O;m2:O.[OH-].[Li+], Reagents are:m1_m5:C1CCOC1.CO.O;m0_m6:C(Cl)(Cl)Cl, and Products are 0:O1C(CCCC1)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (106 mg, 0.47 mmol, prepared in example 11) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.57 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with tert-butyl methyl ether (10 mL) and water (10 mL). Extract with tert-butyl methyl ether (2×10 mL). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2.5 g, 1.7×2.5 cm column, 50% ethyl acetate/hexane, 150 mL) to provide the title compound (80 mg, 93% yield), [α]20D =+9.9°, (c=0.98, chloroform). |
Here is a chemical reaction formula: Reactants are:m0_m4:C(Cl)(Cl)Cl;m2_m3:C(C)N(CC)CC;m2_m3:C(C)(=O)OC=C;m1_m5:C(C)(C)(C)O[C@H]1C=C[C@H](C1)O, Reagents are:m1_m5:COC(C)(C)C, and Products are 0:C(C)(C)(C)O[C@H]1C=C[C@H](C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-4-tert-butyloxy-cyclopent-2-enol (485 mg, 3.1 mmol, prepared in example 9) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.7 eq), pancreatin (3 wt eq, available from Sigma Chemical Company), and vinyl acetate (5 eq). The reaction is allowed to stir for 17 hours at room temperature. The reaction is then filtered through diatomaceous earth and the filtrate is concentrated under vacuum. The products are separated by chromatography on silica gel (10% to 20% ethyl acetate/hexane) to provide (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (B, 50% yield, 76% ee), [α]D =-10.9°, (c=0.98, chloroform), 1H NMR (CDCl3) δ5.94 (d, 1H, J=5.5 Hz), 5.89 (d, 1H, J=5.5 Hz), 5.46 (appt, 1H, J=5.5 Hz), 4.52 (appt, 1H, J=5.5 Hz), 2.8 (m, 1H), 2.0 (s, 3H), 1.6 (d appt, 1H, J=4.8, 14 Hz), 1.22 (s, 9H); 13C NMR (CDCl3) δ171.2, 138.6, 131.6, 77.4, 77.2, 41, 28.7, 28.6, 21.4; IR (neat) νmax 2976, 1738, 1364, 1242, 1196, 1067, 1020 cm-1 ; CIMS m/e (% relative intensity) 199 (M+H+, 4), 139 (M+H+ -AcOH, 70), 83 (100), and (-)-cis-4-tert-butyloxy-cyclopent-2-enol (A, 194 mg, 40% yield, >98% ee), [α]D 17.2°, (c=1.09, chloroform) as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:O.[OH-].[Li+];m3:O;m0_m4:C(Cl)(Cl)Cl;m1_m5:C(C)(C)(C)O[C@H]1C=C[C@H](C1)OC(C)=O, Reagents are:m1_m5:C1CCOC1.CO.O, and Products are 0:C(C)(C)(C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (90 mg, 0.45 mmol, prepared in example 14) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (23.7 mg) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column) to provide the title compound (71 mg, quantitative yield, 76% ee) as a pale yellow oil, [α]20 D =+14.6°, (c=1.03, chloroform). |
Here is a chemical reaction formula: Reactants are:m3_m4:C(C)N(CC)CC;m3_m4:C(C)(=O)OC=C;m0_m5_m1_m6:C(Cl)(Cl)Cl;m0_m5_m1_m6:C(Cl)(Cl)Cl;m2_m7:C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O, Reagents are:m2_m7:COC(C)(C)C, and Products are 0:C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O;0:C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-4-benzyloxy-cyclopent-2-enol (500 mg, prepared in example 16) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.7 eq), pancreatin (3 wt eq, available from Sigma Chemical Company), and vinyl acetate (5 eq). The reaction is allowed to stir for 7 hours at room temperature. The reaction is then filtered through diatomaceous earth and the filtrate is concentrated under vacuum. The products are separated by chromatography on silica gel (20% ethyl acetate/hexane) to provide (-)-cis-4-benzyloxy-cyclopent-2-enol (A) (147 mg, 29% yield) [α]20D -12°, (c=1.09, chloroform), and (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (B) (427 mg, 70% yield),[α]20D =-5.2°, (c=0.97, chloroform), 1 H NMR (CDCl3) δ 7.3 (m, 5H), 6.13 (d, 1H, J=5 Hz), 5.99 (d, 1H, J=5 Hz), 5.5 (m, 1H), 4.59 (d, 1H, J=11.8 Hz), 4.54 (d, 1H, J=11.8 Hz), 4.5 (m, 1H), 2.78 (d appt, 1H, J=7.2, 14.3 Hz), 2.05 (s, 3H), 1.76 (d appt, 1H, J=4.4, 14.3 Hz); 13C NMR (CDCl3) δ171.1, 138.5, 136.4, 133.1, 128.7, 128, 127.9, 81.4, 77.1, 71.2, 37.8, 21.4. |
Here is a chemical reaction formula: Reactants are:m1_m5:C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)OC(C)=O;m3:O;m2:O.[OH-].[Li+];m0_m4:C(Cl)(Cl)Cl, Reagents are:m1_m5:C1CCOC1.CO.O, and Products are 0:C(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (158 mg, 0.68 mmol, prepared in example 17) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.75 mmol) with stirring. After stirring for about 2 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 2 g, 20% ethyl acetate/hexane, 1.5×2.5 cm column) to provide the title compound (120 mg, 92% yield), [α]20D =+5.0°, (C=0.93, chloroform). |
Here is a chemical reaction formula: Reactants are:m3:C(C)OCC;m2:C(C)(=O)OC(C)=O;m1_m5:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O;m0_m4:C(C)(=O)OCC.CCCCCC, Reagents are:m1_m5:N1=CC=CC=C1, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (1 g, 4.67 mmol, prepared in example 10) in pyridine (20 mL) and treat with acetic anhydride (2 mL). Stir the reaction overnight. Dilute the reaction with diethyl ether (100 mL), wash with 3M hydrochloric acid (3×100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum to provide the title compound (1 g, 98% yield) Rf =0.5 (5% ethyl acetate/hexane) [α]20D =+1.3°, (c=1.00, chloroform), 1H NMR (CDCl3)δ5.9 (m, 1H), 5.5 (m, 1H), 4.7 (m, 1H), 2.8 (m, 1H), 2.05 (s, 3H), 1.6 (m, 1H), 0.91 (s, 9H), 0.09 (s, 6H); 13C NMR (CDCl3) δ170.8, 138.8, 131.1, 76.9, 74.8, 41.1, 25.8, 21.1, 18.1, -4.7, -4.6; IR (neat) νmax 2955, 2932, 2859, 1739, 1369, 1240, 1105, 1062, 1049 cm-1 ; CIMS m/e (% relative intensity) 256 (M+H+, 7), 197 (M+H+ --AcOH, 100). |
Here is a chemical reaction formula: Reactants are:m1_m5:O1C(CCCC1)O[C@H]1C=C[C@H](C1)O;m4:C(C)(=O)OCC;m2_m3:C(C)(=O)OC(C)=O;m2_m3:CN(C)C1=NC=CC=C1, Reagents are:m1_m5:N1=CC=CC=C1, and Products are 0:O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (292 mg, 1.59 mmol, prepared in example 11) in pyridine (2.8 mL) and treat with acetic anhydride (0.39 mL) and dimethylaminopyridine (16 mg). Stir the reaction overnight. Concentrate the reaction under vacuum, dissolve the residue with ethyl acetate (10 mL). Wash with 0.5M hydrochloric acid that is 1/2 saturated with brine (2×10 mL), saturated sodium bicarbonate (10 mL), brine (10 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane) to provide the title compound (290 mg, 81%). |
Here is a chemical reaction formula: Reactants are:m3:C([O-])([O-])=O;m4:C([O-])(O)=O;m2:C1(=CC=C(C=C1)S(=O)(=O)O)C;m1_m5:O1C(CCCC1)O[C@H]1C=C[C@H](C1)OC(C)=O, Reagents are:m1_m5:C(C)O;m0_m6:C(Cl)(Cl)Cl, and Products are 0:C(C)(=O)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (192 mg, 0.85 mmol, prepared in example 11) in ethanol (1.5 mL) and treat with p-toluenesulfonic acid (11.7 mg). Stir the reaction at room temperature for 2 hours. Add carbonate or bicarbonate to neutralize the reaction mixture and concentrate under vacuum. Purify the residue by chromatography (silica gel, 3 g, 1.5×3 cm column, 33% ethyl acetate/hexane, 80 mL), to provide the title compound (90 mg, 75% yield, 91% ee), [α]20 D =-66.1°, (c=0.63, chloroform). |
Here is a chemical reaction formula: Reactants are:m2:C(C)N(CC)CC;m1_m3:C(C)(=O)O[C@H]1C=C[C@H](C1)O, Reagents are:m1_m3:C(C)O;m4:[Ni], and Products are 0:C(C)(=O)O[C@H]1C[C@H](CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-cis-4-acetoxy-cyclopent-2-enol (11.0 g, 77.4 mmol, prepared in example 19) in ethanol (50 mL) and treat with Raney nickel (1.1 g, previously washed with water (2×50 mL) and ethanol (2×50 mL), Ra--Ni). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 20 minutes, filter the solution and treat the filtrate with triethylamine (1.0 mL, 7.2 mmol). After one hour concentrate the solution under vacuum and distill the residue by Kugelrohr distillation (60°-80° C., 1 mm Hg), to provide the title compound (9.74 g, 87%) as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m3:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O;m2:[BH4-].[Na+], Reagents are:m1_m3:C(C)O;m4:[Ni], and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (28.85 g, 135 mmol, prepared in example 10) in ethanol (75 mL) and treated with Raney nickel (1.85 g, 32 mmol, previously washed with water (2×50 mL) and ethanol (2×50 mL)). Charge the atmosphere with hydrogen at 50 psi (344.74 kPa) and shake the mixture. After 5.25 hours, filter the reaction. Cool the filtrate to 0° C. and treat with sodium borohydride (0.54 g, 14.3 mmol). After stirring for 2 hours, concentrate the solution under vacuum and distill the resulting oil by Kugelrohr distillation (40°-60° C., 1 mmHg) to provide the title compound (25.5 g, 87%) as a colorless oil, [α]20 =-3.9°, (c=0.99, chloroform); 1H NMR (CDCl3) δ4.4 (m, 1H), 4.3 (m, 1H), 3.03 (d, 1H, J=10.5 Hz), 1.9-1.6 (m, 6H), 0.89 (s, 9H), 0.07 (s, 6H); 13C NMR (CDCl3) δ74.9, 74.1, 44.4, 34.2, 34.1, 25.8, 17.9, -4.9, -5.0; IR (neat) νmax 3405, 2957, 2932, 2888, 2858, 1256, 1091, 1069, 1038, 1026 cm-1 ; CIMS m/e (% relative intensity) 217 (M+H+ 81), 199 (M+H+ --H2O, 37) 67 (100). This (-)-enantiomer (title compound) could not be separated from the (+)-enantiomer (antipode) using the previously described chiral column. |
Here is a chemical reaction formula: Reactants are:m2:CS(=O)(=O)Cl;m3:C(C)N(CC)CC;m1_m4:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O, Reagents are:m1_m4:COC(C)(C)C, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)OS(=O)(=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve (-)-cis-3-tert-butyldimethylsilyloxy-cyclopentanol (9.20 g, 42.5 mmol) in anhydrous tert-butyl methyl ether (50 mL) and cool to -5° C. Treat the solution with methanesulfonyl chloride (3.6 g, 46.5 mmol, mesyl chloride), followed by triethylamine (7.2 mL, 51.7 mmol), at such a rate as to keep the temperature between -5° C. and -2° C. with an ice bath. The ice bath is removed and the solution is stirred for 2 hours. The mixture is then transferred to a separatory funnel and treated with brine/water (50 mL/50 mL). The layers are separated and the aqueous layer is extracted with tert-butyl methyl ether (2×50 mL). The organic layer and extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (12.1 g, 97% yield) as a colorless oil; 1 H NMR (CDCl3) δ5.1 (m, 1H), 4.2 (m, 1H), 2.99 (s, 3H), 2.3 (m, 1H), 2.0 (m, 3H), 1.8 (m, 2H), 0.88 (s, 9H), 0.05 (s, 6H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl;m1_m4_m2_m3:N12CCCCCC2=NCCC1;m1_m4_m2_m3:OC1C=CC(C1)=O, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of trityl chloride (3.44 g, 12.3 mmol) in methylene chloride (20 mL) is treated sequentially with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.2 mL, 14.7 mmol, DBU) and 4-hydroxy-2-cyclopentenone (1.01 g, 10.0 mmol, in 5 mL of methylene chloride, prepared in example 1). The reaction is stirred for 3 days at room temperature and then poured onto ice (approximately 25 mL). The phases are separated and the organic phase is washed with water (25 mL). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 10-20% ethyl acetate/hexane) to provide the title compound (1.26 g, 36%) as a pale yellow oil; 1H NMR (CDCl3) δ7.5 (m, 6H), 7.3 (m, 9H), 6.85 (dd, 1H), 6.05 (d, 1H), 4.8 (m, 1H), 2.1 (m, 2H); 13C NMR (CDCl3) δ206.6, 162.9, 144.3, 135.2, 128.8, 128.4, 127.7, 88.2, 73.1, 43.4; IR (KBr) νmax 3061, 1719, 1491, 1449, 1352, 1181, 1107, 1053 cm-1. |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:[H-].[Al+3].[Li+].[H-].[H-].[H-];m2_m3_m4:[I-].[Li+];m2_m3_m4:COC(C)(C)C;m1_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OC1C=CC(C1)=O, Reagents are:m1_m5:C1(=CC=CC=C1)C, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of 4-trityloxy-2-cyclopentenone (1.03 g, 3.03 mmol, prepared in example 27) in toluene (8 mL) is cooled to -20° C. and treated sequentially with lithium aluminum hydride (76 mg, 2.0 mL), lithium iodide (1.06 g, 7.9 mmol) and dropwise with tert-butyl methyl ether (2 mL, over 5 minutes). The reaction is stirred for 1 hour at -20° C., warmed to 0° C. over 30 minutes, and stirred at 0° C. to 15° C. for 4 hours. The reaction is quenched by slow addition of 1N NaOH (2 mL) and then the reaction is filtered. The solids are washed with tert-butyl methyl ether and the phases of the filtrate are separated. The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound as a white foam (980 mg, 95%). 1H NMR (CDCl3) δ7.5 (m, 6H), 7.3 (m, 9H), 5.79 (d, 1H), 5.14 (d, 1H), 4.5 (m, 1H), 4.4 (m, 1H), 2.2 (m, 1H), 1.42 (d, 1H); 13C NMR (CDCl3) δ145.1, 136.2, 135.9, 129.0, 128.1, 127.3, 87.7, 77.4, 74.9, 43.2; IR (KBr) νmax 3422, 3057, 1491, 1364, 1084, 1065, 1024 cm-1. |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, Reagents are:m3:CO;m4:CO, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Combine (+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (2.50 g, 11.6 mmol, prepared in example 3) and Ni2B (8.5 mL of a 0.14M slurry in methanol, 10 mol %) in methanol (14 mL). Stir the slurry under an atmosphere of hydrogen for 18.5 hours. Then replace the hydrogen atmosphere with nitrogen, filter through diatomaceous earth and rinse the solids with methanol (50 mL). Concentrate the filtrate under vacuum (15 mmHg/40° C.) and purify the residue by Kugelrohr distillation (0.6 mmHg/60°-65° C.) to provide the title compound as a colorless oil (2.31 g, 92%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@H](CC1)O;m1_m2_m3_m4:C(C)N(CC)CC;m1_m2_m3_m4:C(C)(=O)OC=C, Reagents are:m1_m2_m3_m4:COC(C)(C)C, and Products are 0:C(C)(=O)O[C@H]1C[C@H](CC1)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Combine (+/-)-cis-3-tert-butyldimethylsilyloxycyclopentanol (2.119 g, 9.8 mmol, prepared in example 29), pancreatin (6.2 g, 3 weight equivalents), triethylamine (0.9 mL, 6.5 mmol) and vinyl acetate (4.3 mL) in tert-butyl methyl ether (12 mL) and stir for 27 hours at room temperature. Then filter the reaction through diatomaceous earth and concentrate the filtrate under vacuum (room temperature/15 mmHg). Purify the residue by column chromatography [silica gel, 55 g, hexane (300 mL) followed by 5% ethyl acetate/hexane (500 mL)] to provide the (1R,3S)-(+)-3-tert-butyldimethylsilyloxycyclopentanyl acetate (1.23 g, 49% yield, 98% ee as determined from gas chromatography with a chiral column) and (1S,3R)-(-)-3-tert-butyldimethylsilyloxycyclopentanol (771 mg, 37% yield, 92% ee as determined from its acetate derivative followed by GC chiral column analysis, see example 30a). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:FC1=C(C(O)=CC=C1)O;m1_m2_m5:C(C=O)(=O)O;m3_m6:[OH-].[Na+];m4:Cl, Reagents are:m1_m2_m5:O;m3_m6:O, and Products are 0:FC1=C(C(=C(C=C1)C(C(=O)O)O)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 51.2 g of 3-fluorocatechol and 36.8 g of glyoxylic acid were dissolved at 20° C. in 160 ml of water and 34.8 g of sodium hydroxide in solution in 400 ml of water were added to this solution cooled to 0° C. The mixture was heated for 4 hours at 46° C., then cooled to 0° C. and the pH was brought to 4.6 by the addition of concentrated hydrochloric acid. Extraction was carried out with ethyl ether (after evaporation 14.7 g of the starting 9-fluorocatechol were collected) and the aqueous phase was acidified with concentrated hydrochloric acid until a pH of 1.8 was obtained. Extraction was carried out with ethyl acetate and after evaporation of the solvent, 47.7 g of the desired product were obtained (mixture of isomers, 2,3-bis-hydroxy-4-fluoro; 3,4-bis-hydroxy-5-fluoro; 2-fluoro-3,4-bis-hydroxy) which was used as is in Step A of Example 16. |
Here is a chemical reaction formula: Reactants are:m1:O(N)C(C(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=C(C(=C1)OCOCCOC)OCOCCOC)F;m2:O=C(C(=O)O)C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m3:CO, and Products are 0:FC=1C=C(C=C(C1OCOCCOC)OCOCCOC)C(C(OC(C1=CC=CC=C1)C1=CC=CC=C1)=O)ON=C(C(=O)O)C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.640 g of the product of Step D and and 0.474 g of oxo-[2-[(triphenylmethyl)-amino]-thiazol-4-yl]-acetic acid (Belgian Patent Application No. 864,828) were stirred for 4 and a half hours under nitrogen and at ambient temperature in the presence of 20 ml of methanol. Then, the solvent was eliminated, and the residue was chromatographed on silica, eluting with a dichloromethane-methanol (95-5) mixture to obtain 0.612 g of the expected product with a Rf=0.35 [eluant: dichloromethane-methanol (9-1)]. |
Here is a chemical reaction formula: Reactants are:m2:[H-].C(C(C)C)[Al+]CC(C)C;m1:ClC1=C(C=CC(=O)[O-])C=C(C(=C1Cl)OCOCCOC)OCOCCOC, Reagents are:, and Products are 0:ClC1=C(C=C)C=C(C(=C1Cl)OCOCCOC)OCOCCOC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Stage C of Example 40, 20 g of ester of Step B and 88 ml of diisobutylaluminium hydride were reacted to obtain 17.9 g of the expected product melting at 60° C. |
Here is a chemical reaction formula: Reactants are:m1:ClC1=C(C=C)C=C(C(=C1Cl)OCOCCOC)OCOCCOC;m2:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m0_m3:C1CCCCC1.C(C)(=O)OCC, and Products are 0:ClC12C(C=C)(C=C(C(=C1Cl)OCOCCOC)OCOCCOC)O2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Stage D of Example 40, 13.2 g of thee allylic alcohol of Step C and 10.3 g of m-chloro perbenzoic acid were reacted to obtain 13.7 g of the expected product with a Rf=0.25 (AcOEt-cyclohexane 6-4). |
Here is a chemical reaction formula: Reactants are:m3_m6:C(OCC)(OCC)=O;m4:Cl;m1_m2_m5:BrCCCCCCCC;m1_m2_m5:[Mg], Reagents are:m3_m6:C(C)OCC;m1_m2_m5:C(C)OCC, and Products are 0:C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one hour at 30° C., then the mixture is slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether is evaporated off to give tri-n-octylcarbinol. One mole of tri-n-octylcarbinol is added to a mixture of 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride is evaporated off. One mole of tri-n-octylmethylchloride is added to 0.75 liters of methylene chloride and the solution is blanketed with nitrogen and is cooled to 0° C. 0.33 moles of trimethylaluminum is then added and the mixture is allowed to warm to room temperature. The mixture is slowly quenched with 50 ml of water followed by washing with 1 liter of a 10% HCl solution. The organic layer is dried with magnesium sulfate and the solvent is evaporated to give tri-n-octylmethylmethane. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m4_m6:C(CCCCCCC)C(CCCCCCCC)(CCCCCCCC)Cl;m1_m7_m2:C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC;m1_m7_m2:[Cl-].[Ca+2].[Cl-];m5:C[Al](C)C, Reagents are:m4_m6:C(Cl)Cl;m1_m7_m2:C(Cl)Cl, and Products are 0:C(CCCCCCC)C(C)(CCCCCCCC)CCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one hour at 30° C., then the mixture is slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether is evaporated off to give tri-n-octylcarbinol. One mole of tri-n-octylcarbinol is added to a mixture of 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride is evaporated off. One mole of tri-n-octylmethylchloride is added to 0.75 liters of methylene chloride and the solution is blanketed with nitrogen and is cooled to 0° C. 0.33 moles of trimethylaluminum is then added and the mixture is allowed to warm to room temperature. The mixture is slowly quenched with 50 ml of water followed by washing with 1 liter of a 10% HCl solution. The organic layer is dried with magnesium sulfate and the solvent is evaporated to give tri-n-octylmethylmethane. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m3_m6:C(OCC)(OCC)=O;m1_m2_m5:BrCCCCCCCCCC;m1_m2_m5:[Mg], Reagents are:m3_m6:C(C)OCC;m1_m2_m5:C(C)OCC, and Products are 0:C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Three moles of 1-bromodecane was slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether was slowly added to the mixture. After stirring for one hour at 30° C., the mixture was slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer was dried with magnesium sulfate and the ethyl ether evaporated off to give tri-n-decylcarbinol. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m1_m4_m2:C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC;m1_m4_m2:[Cl-].[Ca+2].[Cl-], Reagents are:m1_m4_m2:C(Cl)Cl, and Products are 0:C(CCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: One mole of tri-n-decylcarbinol was added to a mixture of 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas was slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride evaporated off to give a 90% yield of tri-n-decylmethylchloride. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(CCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)Cl;m2:C[Al](C)C, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: One mole of tri-n-decylmethylchloride was added to 0.75 liters of methylene chloride and the solution was blanketed with nitrogen and cooled to 0° C. 0.33 moles of trimethylaluminum was then added and the mixture was allowed to warm to room temperature. The mixture was slowly quenched with 50 ml of water followed by washing with 1 liter of a 10% HCl solution. The organic layer was dried with magnesium sulfate and the solvent was evaporated to give tri-n-decylmethylmethane after vacuum distillation at 225 C/0.5 torr. The yield was 75%. |
Here is a chemical reaction formula: Reactants are:m2:C[Al](C)C;m1_m4:C(CCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCC, Reagents are:m1_m4:C(Cl)Cl;m3:[Ti](Cl)(Cl)(Cl)Cl, and Products are 0:C(CCCCCCCCC)C(C)(CCCCCCCCCC)CCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Alternatively, the 0.1 moles of the synthesized tri-n-decylcarbinol was added to 0.2 liters of methylene chloride. The mixture was covered with a blanket of nitrogen and cooled to 0° C. 0.050 mole titanium tetrachloride was added to the mixture and the solution was stirred 2-3 hours at 0° C. 0.066 mole trimethylaluminum was added and the mixture was allowed to warm to room temperature. The reaction was quenched with water and washed with 0.1 liter of a 20% HCl solution. The organic layer was dried with magnesium sulfate and the methylene chloride removed to give a yield of 70% tri-n-decylmethylmethane. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m5:C(CCCCCCC)Br;m1_m2_m5:[Mg];m3_m6:C(OCC)(OCC)=O, Reagents are:m1_m2_m5:C(C)OCC;m3_m6:C(C)OCC, and Products are 0:C(CCCCCCC)C(O)(CCCCCCCC)CCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: This compound may be prepared in the following manner. Three moles of n-octylbromide are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one hour at 30° C., then the mixture is slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether is evaporated off to give tri-n-octylcarbinol. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m5_m2_m6:C(CCCCCCCCC)[Mg]Br;m1_m5_m2_m6:C(C)OC(OCC)=O;m3:C(CCCCCCCCCCCCC)[Mg]Br, Reagents are:m1_m5_m2_m6:C(C)OCC;m1_m5_m2_m6:C(C)OCC, and Products are 0:C(CCCCCCCCC)C(O)(CCCCCCCCCCCCCC)CCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Decylmagnesium bromide (0.66 mole) in ethyl ether is slowly added to 0.33 moles of diethylcarbonate in 100 ml ethyl ether and stirred for one hour at 30° C. (nitrogen atmosphere). Tetradecylmagnesium bromide (0.33 moles) is slowly added to the solution and stirred for one hour at 30° C. The mixture is then slowly poured into 600 ml of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether evaporated off to give di-n-decyl-n-tetradecylcarbinol. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m1_m4_m2:C(CCCCCCCCC)C(O)(CCCCCCCCCCCCCC)CCCCCCCCCC;m1_m4_m2:[Cl-].[Ca+2].[Cl-], Reagents are:m1_m4_m2:C(Cl)Cl, and Products are 0:C(CCCCCCCCC)C(CCCCCCCCCCCCCC)(CCCCCCCCCC)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: One mole of di-n-decyl-n-tetradecylcarbinol is added to 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride is evaporated off to give di-n-decyl-n-tetradecyl-methylchloride. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m4:C(CCCCCCCCC)[Mg]Br;m1_m6_m2_m7:C(CCCCCCCCCCCCCCCCCC)[Mg]Br;m1_m6_m2_m7:C(C)OC(OCC)=O;m3:C(CCCCCCCCCCCCC)[Mg]Br, Reagents are:m1_m6_m2_m7:C(C)OCC;m1_m6_m2_m7:C(C)OCC, and Products are 0:C(CCCCCCCCCCCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Nonadecylmagnesium bromide (0.33 moles) in ethyl ether is slowly added to 0.33 mole of diethylcarbonate in 100 ml diethyl ether and stirred for one hour at 30° C. (nitrogen atmosphere). n-Tetradecylmagnesium bromide (0.33 mole) is slowly added to the solution and stirred for one hour at 30° C. n-Decylmagnesium bromide (0.33 mole) is slowly added to the solution and stirred for one hour at 30° C. The mixture is then slowly poured into 600 ml of a cold 10% HCl solution. The organic layer is dried with magnasium sulfate and the ethyl ether evaporated off to give n-nonadecyl-n-tetradecyl-n-decylcarbinol. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:C(CCCCCCCCCCCCCCCCCC)C(O)(CCCCCCCCCC)CCCCCCCCCCCCCC;m1_m4_m2:[Cl-].[Ca+2].[Cl-];m3:Cl, Reagents are:m1_m4_m2:C(Cl)Cl, and Products are 0:C(CCCCCCCCCCCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCCCCCC)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: One mole of n-nonadecyl-n-tetradecyl-n-decylcarbinol is added to 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride is evaporated off to give n-nonadecyl-n-tetradecyl-n-decylmethylchloride. |
Here is a chemical reaction formula: Reactants are:m1_m4:CC1(OC2=C(O1)C(=C1C(OC(O1)(C)C)=C2)C(=O)O)C;m3:CI;m2:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m4:CN(C)C=O, and Products are 0:COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic acid (10.0 g, 38.0 mmol) was dissolved in dry DMF (100 mL). Potassium carbonate (15.2 g, 110.0 mmol) was added and the reaction was heated to 55° C. for 30 min. After cooling to ambient temperature, methyl iodide (15.6 g, 110.0 mmol) was added and the solution was stirred overnight. The precipitate was filtered off and the solution was evaporated. The residue was dissolved in saturated aqueous NaHCO3 and ether. The aqueous layer was discarded and the organic phase was dried (Na2SO4), filtered and evaporated to give 9.4 g (88%) of the pure product. |
Here is a chemical reaction formula: Reactants are:m1:CC1(SC2=C(S1)C=C1C(SC(S1)(C)C)=C2)C;m2:C(CCC)[Li];m3:COC(=O)C1=C2C(OC(O2)(C)C)=CC2=C1OC(O2)(C)C, Reagents are:m4:C1CCOC1, and Products are 0:CC1(SC2=C(S1)C(=C1C(SC(S1)(C)C)=C2)C(O)(C2=C1C(OC(O1)(C)C)=CC1=C2OC(O1)(C)C)C1=C2C(SC(S2)(C)C)=CC2=C1SC(S2)(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole (2.86 g, 10 mmol; prepared according to WO-91/12024) was dissolved in anhydrous THF (75 mL) and cooled to -70° C. n-Butyllithium (4.4 mL, 2.5M in hexane) was added. The reaction mixture was allowed to reach ambient temperature. 4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d')-bis-(1,3)-dioxole (1.4 g, 5 mmol) was added as a solid. After 1 hour, the mixture was quenched with saturated aqueous NaH2PO4. The aqueous phase was discarded and the organic layer evaporated. The residue was dissolved in dichloromethane, washed with water and dried (Na2SO4). The product was purified by column chromatography (dichloromethane:heptane, 1:1) giving 1.8 g (44%) of pure product. |
Here is a chemical reaction formula: Reactants are:m2_m4:OCCNCCO;m1_m3:ClC(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)C(=O)Cl)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)C(=O)Cl)(C)C, Reagents are:m2_m4:O;m1_m3:C1=CC=CC=C1, and Products are 0:OCCN(C(=O)C1=C2C(SC(O2)(C)C)=C(C=2SC(OC21)(C)C)C(O)(C2=C1SC(OC1=C(C1=C2SC(O1)(C)C)C(=O)N(CCO)CCO)(C)C)C1=C2SC(OC2=C(C2=C1SC(O2)(C)C)C(=O)N(CCO)CCO)(C)C)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Tris-(8-chlorocarbonyl-2,2,6,6-tetramethyl-benzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.80 g, 0.80 mmol) was dissolved in benzene (200 mL). A solution of of bis(2-hydroxyethyl)amine (8.0 g, 48 mmol) in water (200 mL) was added and after vigorous stirring overnight, the mixture was transferred to a separatory funnel. The aqueous layer was removed and the remaining solid plus the benzene layer was evaporated, dissolved in methanol and passed through a short column (neutral alumina). After elution of unwanted materials with acetonitrile, the amide was eluted with methanol. After evaporation, the product was stirred with water (50 mL) at 40° C. for 2 h and then isolated by filtration. After drying, 0.60 g (60%) of the pure amide was obtained. |
Here is a chemical reaction formula: Reactants are:m5:CN(C=O)C;m1_m2:C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)Br)(C)C)C;m1_m2:C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)Br)(C)C)C;m6:C(=O)=O;m7_m3_m4:[Li]C(C)(C)C;m7_m3_m4:CCCCC, Reagents are:m8:C(C)OC(C)=O;m7_m3_m4:C1CCOC1, and Products are 0:C1(=CC=C(C=C1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:CC=1SC=CC1;m1_m5_m2:[Li]CCCC;m3_m4:CC1(CCC(C2=CC(=CC=C12)Br)=O)C;m3_m4:CC1(CCC(C2=CC(=CC=C12)Br)=O)C, Reagents are:m1_m5_m2:C1CCOC1;m6:C1CCOC1;m7:CCOCC.C(C)OC(C)=O, and Products are 0:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2-methylthiophene (800 mg, 8.1 mmol) in THF (10 mL) was added n-BuLi (1.6M solution in hexane, 5 mL). The mixture was stirred for 1.5 hours and transferred to a cold (-78° C.) flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.63 g, 6.5 mmol), in THF (15 mL). The mixture was gradually warmed to 0° C. The reaction mixture was diluted with ether:ethylacetate (1:1, 80 mL), washed with water (10 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by evaporation. The crude material was dissolved in dichloroethane (20 mL) and pTSA (40 mg) was added. The mixture was stirred at ambient temperature for 16 hours and at 50° C. for 4 hours. The reaction mixture was diluted with ether (150 mL), washed with aqueous 10% NaHCO3 (10 mL), brine (10 mL) and dried with MgSO4. Purification by chromatography on silica gel gave 1.35 g of the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m5:CN(C)C=O;m6:C(=O)=O;m1_m2_m7_m3_m4:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C;m1_m2_m7_m3_m4:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)Br)(C)C;m1_m2_m7_m3_m4:[Li]C(C)(C)C;m1_m2_m7_m3_m4:CCCCC, Reagents are:m8:CCOCC;m1_m2_m7_m3_m4:C1CCOC1, and Products are 0:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m6_m3:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m6_m3:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m6_m3:[Li]CCCC;m4_m5_m7:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C;m4_m5_m7:CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C, Reagents are:m1_m2_m6_m3:C1CCOC1;m4_m5_m7:C1CCOC1;m8:CCOCC, and Products are 0:COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C=1SC(=CC1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 1.4 g, 3.6 mmol), in THF (20 mL) was added n-BuLi (1.6M solution in hexane, 2.5 mL, 4 mmol). The mixture was stirred for 20 minutes at -78° C. and 10 min. at -10° C. The reaction mixture was recooled to -78° C. and 1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde (Compound G, 650 mg, 2.3 mmol) in THF (4 mL) was added to it. The mixture was stirred for 2 hours at -10° C. and diluted with ether (100 mL), washed with brine (10 mL) dried with MgSO4 and the solvent was removed by distillation to to afford a cis and trans (E and Z) isomeric mixture. Purification by chromatography on silica gel of the crude material afforded the title compound as an off (~ 90% purity). |
Here is a chemical reaction formula: Reactants are:m6:CC=1C=CC(=CC1)S(=O)(=O)O;m4_m5:CC1(CCC(C2=CC(=CC=C12)Br)=O)C;m4_m5:CC1(CCC(C2=CC(=CC=C12)Br)=O)C;m1_m7_m2_m3:CC1=CC=C(C=N1)Br;m1_m7_m2_m3:[Li]CCCC;m1_m7_m2_m3:CCCCCC, Reagents are:m8:C1CCOC1;m9:C(C)(=O)OCC;m1_m7_m2_m3:C1CCOC1;m10:C(C)(=O)OCC, and Products are 0:CC1=CC=C(C=N1)C1=CCC(C2=CC=C(C=C12)Br)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 6-methyl-3-bromopyridine (890 mg, 5.2 mmol) in THF (15 mL) was added n-BuLi in hexane (1.6M solution, 3.5 mL, 5.6 mmol) and stirred for 1 hour. This mixture was added to a flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.35 g, 5.4 mmol), in THF (5 mL) at -78° C. The reaction mixture was gradually warmed to ambient temperature and stirred for 16 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with water (10 mL), brine (10 mL) and dried with MgSO4. Solvent was removed by distillation, the crude material was dissolved in toluene (25 mL) and pTSA (530 mg, 2.8 mmol) was added. The mixture was heated at 90° C. for 36 hours. Thereafter it was diluted with ethyl acetate (100 mL), washed with 10% NaHCO3 (2×10 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by evaporation. The title compound was obtained by recrystallization from ethyl acetate and hexane mixture (1:9). |
Here is a chemical reaction formula: Reactants are:m6:CC=1C=CC(=CC1)S(=O)(=O)O;m1_m7_m2_m3:BrC1=CC=C(C=C1)C;m1_m7_m2_m3:[Li]C(C)(C)C;m1_m7_m2_m3:CCCCC;m4_m5_m10:CC1(SC2=CC=C(C=C2C(C1)=O)Br)C;m4_m5_m10:CC1(SC2=CC=C(C=C2C(C1)=O)Br)C, Reagents are:m1_m7_m2_m3:C1CCOC1;m8:ClCCl;m9:C(C)OC(C)=O;m4_m5_m10:C1CCOC1, and Products are 0:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 4-bromotoluene (720 mg, 4.2 mmol) in THF (8 mL) was added t-BuLi in pentane (1.7M, 0.5 mL, 0.85 mmol). The mixture was warmed to ambient temperature over 30 minutes with stirring. This mixture was added to a flask containing 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 140 mg, 0.4 mmol) and THF (2 mL). and stirred for 16 hours at ambient temperature. The reaction was quenched by adding aq. NH4Cl, and the resulting mixture was extracted with ethylacetate, washed with brine, dried and the solvent was removed by evaporation. The product was isolated by chromatography on silica gel. The material was dissolved in dichloromethane (5 mL) and pTSA (5 mg) was added and heated to 50° C. for 3 hours. The misture was diluted with ethylacetate (20 mL), washed with 10% NaHCO3 (5 mL), brine (5 mL), dried with MgSO4 and the solvent was removed by evaporation to afford the title compound as an off. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m6:CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C;m1_m2_m5_m3_m6:CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C;m1_m2_m5_m3_m6:[Li]C(C)(C)C;m4:CN(C)C=O, Reagents are:m1_m2_m5_m3_m6:C1CCOC1;m1_m2_m5_m3_m6:CCCCC;m7:C(C)(=O)OCC, and Products are 0:CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene (Compound P, 480 mg, 1.45 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 1.1 mL) and the mixture was stirred for 30 minutes. DMF (200 mg, 2.9 mmol) was added, the mixture was warmed to ambient temperature and stirred for 3 hours. The reaction was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m4_m5_m9:CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C;m4_m5_m9:CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C;m1_m2_m7_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m7_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m7_m3_m8:[Li]CCCC;m6_m12:Cl[Sn](Cl)(Cl)Cl, Reagents are:m10:C(C)(=O)OCC;m4_m5_m9:C1CCOC1;m1_m2_m7_m3_m8:C1CCOC1;m1_m2_m7_m3_m8:CCCCCC;m6_m12:ClCCl;m11:ClCCl, and Products are 0:C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C2=CC=C(C=C2)C)C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 1.4 g, 3.6 mmol) in THF (9 mL) was added n-BuLi in hexane (1.6M solution, 2.8 mL). The mixture was gradually warmed to ambient temperature over 30 minutes and stirred for 5 minutes. To this mixture was added 2,2-dimethyl-4(tol-4-yl)-chrom-3-en-6-al (Compound Q, 260 mg, 0.93 mmol) in THF (1 mL) at ambient temperature and the mixture was stirred for 5 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with brine (10 mL) dried and the solvent was removed by evaporation. The residual material was subjected to flash chromatography on silicagel to obtain the E and Z olefinic compounds, which were dissolved in dichloromethane (5 mL) and cooled to -50° C. A solution of SnCl4 in dichloromethane (150 mg in 0.7 mL) was added to the olefinic compounds. The reaction mixture was gradually warmed to -10° C. over 3hours and then quenched with methanol and water. The reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was washed with brine and dried. Solvent was removed under reduced pressure and the residue purified by chromatography on silicagel to afford the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C;m1_m2_m3_m4:CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C;m1_m2_m3_m4:CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(C=C3)C3=CC=C(C(=O)OCC)C=C3)C;m1_m2_m3_m4:CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(C=C3)C3=CC=C(C(=O)OCC)C=C3)C, Reagents are:, and Products are 0:CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(C=C3)C3=CC=C(C(=O)O)C=C3)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By following the procedure employed for the preparation of 4-[1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid (Compound 4), ethyl 4-[2,2-dimethyl-4-(tol-4-yl)-benzo(1,2-g)-chrom-3-en-7-yl]benzoate (Compound 9, 10 mg, 0.02 mmol), was converted into the title compound using LiOH in water (0.2 mL, 0.2 mmol). The title compound was obtained as an off white solid. |
Here is a chemical reaction formula: Reactants are:m4_m6:CC1(OC2=CC=C(C=C2C(C1)=O)Br)C;m1_m5_m2_m3:CC=1SC=CC1;m1_m5_m2_m3:[Li]CCCC;m1_m5_m2_m3:CCCCCC, Reagents are:m7:C(C)(=O)OCC;m4_m6:C1CCOC1;m1_m5_m2_m3:C1CCOC1, and Products are 0:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2-methylthiophene (820 mg, 8.3 mmol) in THF (16 mL) was added n-BuLi in hexane (1.6M, 4.4 mL, 8.5 mmol). The mixture was warmed to ambient temperature and stirred for 15 minutes. This solution was added to a flask containing cold (-78° C.) solution of 2,2-dimethyl-6-bromo-chroman-4-one (1.08 g, 4.2 mmol) in THF (4 mL). The mixture was stirred and allowed to gradually warm to ambient temperature over 8 hours, and then stirred for an additional 4 hours at ambient temperature. The mixture was diluted with ethyl acetate (200 mL), washed with 10% HCl, brine (20 mL), dried and the solvent was removed by evaporation. The product was purified by chromatography on a silica gel column to afford the title compound as a colorless off. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m6:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C;m1_m2_m5_m3_m6:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C;m1_m2_m5_m3_m6:[Li]C(C)(C)C;m4:CN(C)C=O, Reagents are:m1_m2_m5_m3_m6:C1CCOC1;m1_m2_m5_m3_m6:CCCCC;m7:C(C)(=O)OCC, and Products are 0:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m7_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m7_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m7_m3_m8:[Li]CCCC;m4_m5_m9:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C;m4_m5_m9:CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C;m6_m12:Cl[Sn](Cl)(Cl)Cl, Reagents are:m1_m2_m7_m3_m8:C1CCOC1;m1_m2_m7_m3_m8:CCCCCC;m4_m5_m9:C1CCOC1;m10:C(C)(=O)OCC;m6_m12:ClCCl;m11:ClCCl, and Products are 0:C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 690 mg, 1.75 mmol) in THF (8 mL) was added n-BuLi in hexane (1.6M solution, 1.1 mL). The mixture was gradually warmed to ambient temperature over 30 min and stirred for 5 minutes. The mixture was recooled to -78° C. and 2,2-dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al (Compound S, 300 mg, 1.1 mmol) in THF (1 mL) was added to the reaction mixture. The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with brine (10 mL) dried and the solvent was removed by evaporation. The material was subjected to flash chromatography on silica gel to obtain the E and Z olefinic compounds, which were dissolved in dichloromethane (5 mL) and cooled to -78° C. A solution of SnCl4 in dichloromethane (52 mg in 0.2 mL) was added to the olefinic compounds. The resulting mixture was stirred for 30 minutes, quenched with methanol, water and diluted with ethyl acetate (100 mL). The organic layer was washed with brine and dried. Solvent was removed under reduced pressure and purified by silicagel chromatography to afford the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m5_m3_m6:C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O;m1_m2_m4_m5_m3_m6:C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O;m1_m2_m4_m5_m3_m6:[Li+].[OH-], Reagents are:m1_m2_m4_m5_m3_m6:CO;m1_m2_m4_m5_m3_m6:C1CCOC1;m1_m2_m4_m5_m3_m6:O, and Products are 0:CC1(OC2=CC3=C(C=C2C(=C1)C=1SC(=CC1)C)C=C(C=C3)C3=CC=C(C(=O)O)C=C3)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of ethyl-4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate (Compound 11, 18 mg, 0.03 mmol) in methanol (0.5 mL) and THF (1 mL), was added LiOH in water (1M solution, 0.3 mL). The reaction mixture was stirred for 20 hours, the solvent was removed under reduced pressure, the residue dissolved in water (5 mL), washed with ether (10 mL) and the aqueous layer was acidified to PH 5. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried, and the solvent was removed under reduced pressure to afford the title compound as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are:m3_m4_m7:CC1(SC2=CC=C(C=C2C(C1)=O)Br)C;m3_m4_m7:CC1(SC2=CC=C(C=C2C(C1)=O)Br)C;m1_m5_m2_m6:CC=1SC=CC1;m1_m5_m2_m6:[Li]CCCC, Reagents are:m3_m4_m7:C1CCOC1;m8:CCOCC;m1_m5_m2_m6:C1CCOC1;m1_m5_m2_m6:CCCCCC, and Products are 0:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2-methylthiophene (1.2 g, 12.2 mmol) in THF (8 mL) was added n-BuLi in hexane (1.6M, 8.5 mL). The mixture was warmed to ambient temperature over 30 minutes. with stirring. The mixture was recooled to -78° C. and a solution of 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 1.4 g, 5.2 mmol) in THF (10 mL) was added. The mixture was stirred for 16 hours at ambient temperature. Then the reaction mixture was diluted with ether (125 mL), washed with water (10 mL), brine (10 mL) dried and the solvent was removed by evaporation. The product was seperated by column chromatography and was dissolved in dichloromethane (5 mL). To this solution p-TSA (5 mg) was added and the mixture was stirred at ambient temperature for 5 min. The reaction was quenched with 10% NaHCO3 (3 mL), washed with brine (5 mL), dried and the solvent was removed by distillation. The residual crude material was purified by column chromatography to obtain the title compound as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are:m4:CN(C)C=O;m1_m2_m5_m3_m6:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C;m1_m2_m5_m3_m6:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C;m1_m2_m5_m3_m6:[Li]CCCC, Reagents are:m1_m2_m5_m3_m6:C1CCOC1;m1_m2_m5_m3_m6:CCCCCC, and Products are 0:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2,2-dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene (Compound T, 430 mg, 1.2 mmol) in THF (12 mL) was added n-BuLi in hexane (1.6M solution, 1 mL). The mixture was gradually warmed to ambient temperature over 1 hour and recooled to -78° C. To this solution was added DMF (220 mg, 3 mmol) and the mixture was stirred at ambient temperature for 16 hours. The reaction was quenched by adding water (10 mL) and ethy lacetate (100 mL). The organic layer was washed with brine (10 mL), dried and the solvent was removed by distillation to obtain the title compound as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are:m4_m5_m7:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C;m4_m5_m7:CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C;m4_m5_m7:C1CCOC1;m1_m2_m6_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m6_m3_m8:C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC;m1_m2_m6_m3_m8:C(C)(C)[N-]C(C)C.[Li+];m1_m2_m6_m3_m8:C1CCOC1;m1_m2_m6_m3_m8:C1CCOC1, Reagents are:, and Products are 0:COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C1=CC=C(C=C1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 500 mg, 1.29 mmol) in THF (2.5 mL) was added fleshly prepared lithium diisopropylamide in THF(1.5 mmol). The mixture was allowed to warm to -5° C. over a period of 1 hour and 40 minutes. The reaction mixture was recooled to -78° C. and 2,2-dimethyl-4(2-methyl-thien-5-yl)-thiochrom-3-en-6-al (Compound U, 180 mg, 0.58 mmol) in THF (2 mL) was added. The reaction mixture was gradually warmed to -10° C. over 2 hours. Then the reaction was quenched by adding water (5 mL) and ethyl acetate (70 mL). The organic layer was washed with brine (10 mL) dried and the solvent was removed by distillation. The product E and Z isomers were isolated by column chromatography. The required E (minor) isomer (45 mg) was dissolved in dichloromethane (5 mL) and cooled to -78° C. To this solution SnCl4 (110 mg, 0.42 mmol) in dichloromethane (1 mL) was added dropwise, the reaction mixture was gradually warmed to -30° C. over 30 min. The reaction was quenched by adding ethanol (0.5 mL), water (5 mL) and ethyl acetate (75 mL). The organic layer was washed with brine (10 mL), dried and the solvent was removed by distillation. The title compound was isolated as a white solid after column chromatography. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCC[Si](C)(C)C)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O;m1_m3_m4:C1=CC=CC=C1;m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m5:C(C)N(CC)CC;m1_m3_m4:C(C)(OCC)(OCC)OCC, and Products are 0:C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCC[Si](C)(C)C)O[C@@H]([C@@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](OC(C)=O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of compound 10a (1.87 g), in a mixture of benzene (50 mL) and triethyl orthoacetate (50 mL), containing 4-toluenesulfonic acid (0.25 g) was stirred for 1 h at room temperature. The acid was then neutralized with a few drops of triethylamine, and the mixture evaporated to dryness. The residue was mixed with 80% aqueous acetic acid (100 mL) and the mixture stirred for 40 min at room temperature. Processing as described for 10b (to give 11b), gave the title compound 11a (1.86 g,89%); a white amorphous solid; [α]D -2.7° (c, 1.1, chloroform). 13C NMR (CDCl3): δ171.03 (CH3CO), 166.78, 166.35, 166.18, 165.02 (4×PhCO), 101.27, 101.09 (C-1, C-1'), 98.17 (C-1 fuc), 80.10, 78.20 (C-3, C-4), 74.67, 73.54, 73.30 (3×PhCH2), 67.86 (OCH2CH2Si), 63.31, 61.42 (C-6, C-6'), 21.21 (CH3 CO), 18.47 (OCH2CH2Si), and 17.53 (C-6 fuc); negative ion LSIMS: 1470.8 (M+mNBA)-, 1363.7 (M+NO2)-. |
Here is a chemical reaction formula: Reactants are:m1:C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCCCCCCCC)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O;m4:C1(=CC=C(C=C1)S(=O)(=O)O)C;m2_m3:C1=CC=CC=C1;m2_m3:C(C)C(C([O-])([O-])[O-])(CC)CC, Reagents are:m5:C(C)N(CC)CC, and Products are 0:C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCCCCCCCC)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](OC(C)=O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound 22 (5 g) was dissolved a 1:1 mixture of benzene and triethylorthoacetate (110 mL), containing 4-toluenesulfonic acid (0.2 g), and the mixture was stirred for 1 h at room temperature. The acid was neutralized with triethylamine, and the mixture evaporated to dryness. The residue was dissolved in 80% aqueous acetic acid (75 mL) and stirred for 40 min at room temperature. The acetic acid was evaporated under diminished pressure and the last traces were removed by co-evaporation with toluene to yield 23 (4.7 g, 91.3%); [α]D, -4.5° (c 0.8, chloroform), t.l.c. (5:1 ethyl acetate-toluene). 13C NMR (CDCl3): δ170.98 (COCH3), 166.75, 166.33, 166.18, 165.07 (4×PhCO), 102.03, 101.08 (C-1, C-1'), 98.16 (C-1 fuc), 80.07, 78.23 (C-3, C-4), 74.69, 73.53, 73.24 (3×PhCH2), 70.66 [OCH2 (CH2)6 ], 63.23, 61.42 (C-6, C-6'), 32.25-23.14 [(CH2)6CH3 ], 21.20 (COCH3), 17.49 (C-6 fuc), and 14.63 (CH3). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:CCCCCCCCCCCCCCCCCCOCC(CO)O;m1_m2_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl;m3:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl;m4:C(C)N(CC)CC, Reagents are:m1_m2_m5:C(Cl)Cl, and Products are 0:C(CCCCCCCCCCCCCCCCC)OCC(O)COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 51.69 Grams (150 mmol) of batylalcohol and 62.73 g (225 mmol) freshly recrystallized tritylchloride are dissolved at 35° C. in 350 ml methylene chloride. (Note: It is recommended that the tritylchloride be freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.). During 15 minutes, 22.77 g (225 mmol; 31.38 ml) triethylamine is added dropwise to the stirred solution at 30°-35° C. (cooling with a water bath). The reaction is continued for six hours at ambient temperature. (Note: It is recommended that a control TLC be done to make sure that the reaction is complete). The solution is then washed with 300 ml of a NaHCO3 solution (1%), dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The oily residue (155 g) is dissolved in 660 ml acetonitrile by warming up to 70° C. with stirring. After cooling to room temperature the title product crystallizes (preferentially after adding a few seed crystals). Crystallization is completed by standing overnight at ambient temperature. The crystallizate is filtered off to yield 82.5 g (93.7%) of crude product (m.p. 53°-55° C.) which can be used for the following step without purification. Recrystallization from halpasol (310 ml) yields 71 g (80%) of pure tritylbatylalcohol. B. In a similar way, introduction of the 3-O-trityl function is accomplished for each 1-O-R-glycerol of Example 2-B. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3_m5:[OH-].[K+];m1_m4_m2_m3_m5:ClC=1C(=C(C(=C(C1Cl)Cl)Cl)C#N)C#N;m1_m4_m2_m3_m5:C1(=CC=CC=C1)O, Reagents are:m1_m4_m2_m3_m5:O;m1_m4_m2_m3_m5:CC(=O)C;m6:O, and Products are 0:ClC=1C(=C(C(=C(C1OC1=CC=CC=C1)Cl)Cl)C#N)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of potassium hydroxide (11.2 parts) in water (22 parts) was added dropwise to a stirred solution of 3,4,5,6-tetra-chloro-1,2-dicyanobenzene (26.6 parts) and phenol (9.4 parts) in acetone (100 arts) at 0° C. The solution was stirred at 60° C. for 2 hours before pouring into water (500 parts). The aqueous mixture was extracted with dichloromethane (3×500 parts). The dichloromethane extracts were washed with water (3×200 parts), dried over anhydrous Na2SO4, filtered and the dichloromethane was removed under reduced pressure to leave a brown solid. The solid was recrystallised from butan-1-ol. 3,5,6-Trichloro-1,2-dicyano-4-phenoxybenzene (17 parts) was obtained as a brown solid, m.p. 147°-150° C. |
Here is a chemical reaction formula: Reactants are:m1:C(OC)COC;m2_m3:C1=CC=CC2=CC3=CC=CC=C3C=C12.[K], Reagents are:m2_m3:CN1CCCC1=O, and Products are 0:C1=CC=CC2=CC3=CC=CC=C3C=C12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A KAn solution is prepared as described in Example 20. The monoglyme is allowed to evaporate and the solid potassium anthracide complex collected. The melting point of the potassium anthracide crystals is >300° C. The dark-blue crystals turn white on exposure to air as a result of the radical-anion oxidation. Potassium anthracene salt is added to a solution of anhydrous NMP to give a 0.05M anthracene radical-anion solution resulting in the characteristic deep blue-black coloration of the solution. The KAn is stable in NMP. A sample of PTFE is treated in this bath and Pd seeded and electroless Cu subsequently plated as described in Example 17 with similar results. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1=CC=C(C(=O)OCC)C=C1;m1_m2_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m3:CC(=O)C, Reagents are:m5_m0:CCCCCC.C(C)(=O)OCC, and Products are 0:C(C#CC#CCCCC)OC1=CC=C(C(=O)OCC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a flask were placed 3.78 g (0.024 mole) of 1-chloro-2,4-nonadiyne thus obtained, 3.32 g (0.02 mole) of ethyl 4-hydroxybenzoate, 5.5 g (0.04 mole) of potassium carbonate, and 50 ml of acetone and the mixture was refluxed by heating for 11 hours. After allowing to cool the reaction mixture to room temperature, the reaction mixture was poured in 250 ml of ice-water and the product was extracted with methylene chloride. After distilling off the solvent of the organic layer, the residue formed was purified by a silica gel column chromatography(developing solvent: hexane/ethyl acetate=3/1) to provide 4.0 g (yield 70%) of ethyl 4-(2,4-nonadiynyloxy)-benzoate. |
Here is a chemical reaction formula: Reactants are:m1_m6_m2_m3:FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCCCCCC)F)(F)F;m1_m6_m2_m3:[Cl-].[Li+];m1_m6_m2_m3:CN(C=O)C, Reagents are:m1_m6_m2_m3:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1;m4_m5:C1CCOC1;m4_m5:[Cl-].[Zn+2].[Cl-], and Products are 0:C(CCCCCC)[Si]1(CCC(CC1)C1=CC(=C(C(=C1)F)CC(CC)C)F)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.0 g (20 mmols) of (S)-1-bromo-2-methylbutane was dropped in a mixture of 0.5 g (21 mmols) of magnesium and 50 ml of THF to obtain a Grignard reagent. This reagent was dropped in 20 ml of a THF solution of 2.8 g (20 mmols) of zinc chloride to obtain an organizing reagent. Subsequently, the solution was dropped in a mixture of 10.7 g (20 mmols) of (2,6-difluoro-4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, 100 mg of tetrakis(triphenylphosphine)palladium (0), 500 mg of lithium chloride and 50 ml of N,N-dimethylformamide, and agitated at 50° C. for 8 hours. The reaction mixture was after-treated by a usual manner and purified through chromatography to obtain 6.4 g (yield: 70%) of 4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene. |
Here is a chemical reaction formula: Reactants are:m3_m5:C(CCCCCC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1;m4:O;m1_m2_m6:CC(C)([O-])C.[K+];m1_m2_m6:[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m3_m5:C1CCOC1;m1_m2_m6:C1CCOC1, and Products are 0:C(CCCCCC)[Si]1(CCC(CC1)C=O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 28 g of 4-n-heptyl-4-phenyl-4-silacyclohexanone in 50 ml of THF was added to the solution. After agitation for 2 hours at room temperature, the mixture was poured into iced water and extracted with methylene chloride. The extract was washed, dried and concentrated by a usual manner. n-Hexane was added to the resultant concentrate, followed by removal of the resultant triphenylphosphine oxide crystals by filtration. The resultant filtrate was concentrated. The concentrate was hydrolyzed with 100 ml of 20% hydrochloric acid, followed by washing, drying and concentration by a usual manner to obtain 4-n-heptyl-4-phenyl-4-silacyclohexane carbaldehyde. |
Here is a chemical reaction formula: Reactants are:m3_m5:C(CCCC)[Si]1(CCC(CC1)C1CCC(CC1)=O)C1=CC=CC=C1;m1_m2_m6:CC(C)([O-])C.[K+];m1_m2_m6:[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1;m4:O, Reagents are:m3_m5:C1CCOC1;m1_m2_m6:C1CCOC1, and Products are 0:C(CCCC)[Si]1(CCC(CC1)C1CCC(CC1)C=O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 34 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexanone in 50 ml of THF was added to the ylide solution and agitated at room temperature for 2 hours. Thereafter, the mixture was poured into iced water and extracted with methylene chloride, followed by washing, drying and concentration by a usual manner. n-Hexane was added to the residue, and the resultant crystals of triphenylphosphine oxide were removed by filtration. The filtrate was concentrated, and the resultant residue was hydrolyzed with 100 ml of 20% hydrochloric acid, followed by washing, drying and concentration by a usual manner to obtain 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexane carbaldehyde. |
Here is a chemical reaction formula: Reactants are:m1_m2_m6:CC(C)([O-])C.[K+];m1_m2_m6:[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1;m4:O;m3_m5:C(CC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1, Reagents are:m1_m2_m6:C1CCOC1;m3_m5:C1CCOC1, and Products are 0:C(CC)[Si]1(CCC(CC1)C=O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 23 g of 4-n-propyl-4-phenyl-4-silacyclohexanone in 50 ml of THF was added to the ylide solution and agitated at room temperature for 2 hours. Thereafter, the mixture was poured into iced water and extracted with methylene chloride, followed by washing, drying and concentration by a usual manner. n-Hexane was added to the residue, and the resultant crystals of triphenylphosphine oxide were removed by filtration. The filtrate was concentrated, and the resultant residue was hydrolyzed with 100 ml of 20% hydrochloric acid, followed by washing, drying and concentration by a usual manner to obtain 4-n-propyl-4-phenyl-4-silacyclohexane carbaldehyde. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O;m1_m3_m2:[BH4-].[Na+], Reagents are:m1_m3_m2:CCO;m4:O, and Products are 0:C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 100 mg. (0.303 mmol) of 3-acetoxy-androst-5-en-17-one in 3 ml EtOH at -10° C., was added 22.9 mg (0.606 mmol) of sodium borohydride with stirring. After the reaction mixture was stirred for one and 1/2 hours, the mixture was diluted with 10 ml water, the ethanol solvent removed under vacuum, and the residue extracted with ethyl acetate. The organic layer was washed with aqueous Na2CO3, brine, dried over sodium sulfate and concentrated to leave a residue of crude title compound. Proton NMR confirmed the assigned structure. |
Here is a chemical reaction formula: Reactants are:m1_m5:C#CC1=CC=C(C=C1)O;m4:C([O-])([O-])=O.[Na+].[Na+];m2_m3:O1CCCC=C1;m2_m3:S(O)(O)(=O)=O, Reagents are:m1_m5:C(OC)COC;m6:O, and Products are 0:O1C(CCCC1)OC1=CC=C(C=C)C=C1.OC1=CC=C(C=C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Poly(p-hydroxystyrene) (weight average molecular weight: 9,600) in an amount of 9 g was dissolved in 100 ml of dimethoxyethane, and thereto 12.6 g of 3,4-dihydro-2H-pyran and 0.5 ml of sulfuric acid were added. This solution was stirred for 15 hours at 30°-40° C. After the reaction was completed, the reaction solution was concentrated under reduced pressure. The residue obtained was neutralized with sodium carbonate, and then poured into water to precipitate crystals. The crystals were filtered off, washed with water and dried under reduced pressure. Thus, 11.0 g of poly(p-tetrahydropyranyloxystyrene-p-hydroxystyrene) was obtained as white powder. The ratio of the p-tetrahydropyranyloxystyrene units to the p-hydroxystyrene units in the polymer obtained was determined to be 3:7 by 1H-NMR analysis. |
Here is a chemical reaction formula: Reactants are:m4:O;m5_m1_m2_m3:C(C=C)(=O)OC1OCCCC1;m5_m1_m2_m3:C(C(=C)C)(=O)OC;m5_m1_m2_m3:N(=NC(C#N)(C)C)C(C#N)(C)C, Reagents are:m5_m1_m2_m3:COCC(C)O, and Products are 0:C(C=C)(=O)OC1OCCCC1.C(C(=C)C)(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 80 g of propylene glycol monomethyl ether were dissolved 78 g (0.5 mole) of tetrahydropyranyl acrylate and 42 g (0.5 mole) of methyl methacrylate, and 3 g of azobisisobutyronitrile was added thereto, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, the reaction mixture was dropped into a large amount of water to coagulate a resin. The resin was recovered and dried in a vacuum drier kept at 50° C. overnight to obtain 96 g of a white fine powder of tetrahydropyranyl acrylate/methyl methacrylate copolymer resin. |
Here is a chemical reaction formula: Reactants are:m5_m1:C(C)(C)(C)OC1=CC=C(C=C)C=C1;m4:C(C)(=O)OCC;m2:N(=NC(C#N)(C)C)C(C#N)(C)C;m3:S(O)(O)(=O)=O, Reagents are:m5_m1:COCC(C)O, and Products are 0:C#CC1=CC=C(C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 80 g of propylene glycol monomethyl ether was dissolved 88 g of p-t-butoxystyrene, and then, 2 g of azobisisobutyronitrile was added to the solution, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, an aqueous sulfuric acid solution was added to the reaction mixture and the resulting mixture was subjected to hydrolysis at 80° C. for 8 hours. Subsequently, ethyl acetate was added to the reaction mixture and the resulting mixture was washed with water, after which the solvent was replaced by acetone. The resulting resin solution was dropped into a large amount of water to coagulate a resin. The resin was recovered and dried in a vacuum drier kept at 50° C. overnight to obtain 48 g of a white fine powder of poly(p-hydroxystyrene). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C(=C)C)(=O)OCCN=C=O;m1_m2_m3:NC1=CC=C(C=C1)O, Reagents are:m1_m2_m3:O1CCOCC1, and Products are 0:OC1=CC=C(C=C1)NC(NCCOC(C(=C)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methacryloyloxyethylisocyanate and 4-aminophenol were added to dioxane solvent, and stirred for 2 hours to obtain 2-(N'-(4-hydroxyphenyl)ureido)ethylmethacrylate (hereinafter referred to simply as "Compound 1"). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(=CC=CC=C1)N=C=O;m1_m2_m3:NC1=CC=C(C=C1)O, Reagents are:m1_m2_m3:O1CCOCC1, and Products are 0:C1(=CC=CC=C1)NC(NC1=CC=C(C=C1)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Phenyl isocyanate and 4-aminophenol were added to dioxane solvent, and stirred for 2 hours to obtain 4-(N'-phenylureido)phenol (hereinafter, referred to simply as "Compound 8"). |
Here is a chemical reaction formula: Reactants are:m2:C(C(=C)C)(=O)Cl;m1_m3:C1(O)=CC=C(O)C=C1, Reagents are:m1_m3:CC(=O)C;m4:N1=CC=CC=C1, and Products are 0:C(C(=C)C)(=O)O.C1(O)=CC=C(O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 350 g of hydroquinone was dissolved in 2.5 kg of acetone and 500 ml of pyridine. After cooling to 0° C., 313.5 g of methacryloyl chloride was added dropwise, with the reaction temperature maintained at 0° to 5° C. Stirring was then carried out for 3 hours at the same temperature. After stirring for one more hour at room temperature, the acetone was evaporated. Water was then added, and hydrochloric acid was used to adjust the solution to an acidic pH (pH 4), with ether extraction then performed. After washing this ether layer with a 5% aqueous solution of sodium hydrogencarbonate, the solution was then washed with water and dried (anhydrous sodium carbonate). The ether was then evaporated out, with a white solid being obtained. This was recrystallized from water, to obtain 420 g of colorless, needle crystals of hydroquinone monomethacrylate having a melting point of 120.5° to 121.5° C. |
Here is a chemical reaction formula: Reactants are:m3:C(C)O;m1:OC1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C;m2:S(O)(O)(=O)=O, Reagents are:m4:C(C)(=O)OCC, and Products are 0:OC1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7-Hydroxy-4-methylcoumarin-3-acetic acid (1) (1 gm, 4.3 mmol) was suspended in anhydrous ethanol (15 mL), concentrated sulfuric acid (1.5 mL) was added and the mixture was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with 5% NaHCO3 (5×50 mL), water (2×50 mL), saturated NaCl (2×50 mL) dried with sodium sulfate, filtered and the filtrate was evaporated under reduced pressure to give 1.04 gm (4.0 mmol, 92% yield of 2 as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:C(C)(=O)[C@]1([C@@]([C@]([C@](O[C@@H]1CO)(C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)OCC)C)C(C)=O)(O)C(C)=O)(O)C(C)=O)O;m1_m4_m2:[OH-].[K+];m3:Cl, Reagents are:m1_m4_m2:CO, and Products are 0:[C@@H]1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 7-(tetraacetyl-β-galactosyl)-4-methylcoumarin-3-acetic acid, ethyl ester (3) (422 mg, 0.712 mmol) in methanol was added 6.8M KOH (5 mL) and the solution was stirred overnight at room temperature. The solution was neutralized by the addition of 1N HCl and evaporated to dryness under reduced pressure. The residue was dissolved in water (10 mL) and desalted using C18Sep Pack Cartridges in 10×1 mL portions. The C18Sep Pack Cartridge (Waters Part No. 65910) was washed with methanol (3 mL) and water (3 mL) before the sample was applied in 1 mL. The cartridge was then washed with water (3 mL) to remove any salt followed by metahnol (3 mL) which eluted the desired product as determined by TLC (silica gel, acetone:20 mM NaOAc 9:1). The methanol washes were pooled and evaporated under reduced pressure and the while solid obtained was recrystallized from ethanol/water to give 170 mg (0.43 mmol, 60%) of 4 as white crystals: m.p. 186°-188° C. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2_m5:C1=CC=CC=2C3=CC=CC=C3CC12.[Li];m1_m4_m2_m5:CC(=C1C=CC=C1)C1=CC=CC=C1, Reagents are:m1_m4_m2_m5:O1CCCC1;m1_m4_m2_m5:O1CCCC1, and Products are 0:C1(C=CCC1)C=1C(=C(C=CC1)CC)C1C2=CC=CC=C2C=2C=CC=CC12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 67.8 mmol of lithiumfluorene in 50 cm3 of tetrahydrofuran is added to a solution of 11.4 g (67.8 mmol) of 6-methyl-6-phenyl-fulvene in 40 cm3 of tetrahydrofuran at room temperature. After the mixture had been stirred at room temperature for 2 hours, 60 cm3 of water were added. The substance which precipitated during this procedure was filtered off with suction, washed with diethyl ether and dried under an oil pump vacuum. 19.1 g (84.2%) of 2,2-cyclopentadienyl(9-fluorenyl)-ethylbenzene were obtained (correct elemental analyses; 1H-NMR spectra). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:CCCCCC;m1_m2_m3_m5:C(CCC)[Li];m1_m2_m3_m5:C1=CC=CC=2C3=CC=CC=C3CC12;m4:C1(=CC=CC=C1)C1=C(C(C=C1)=C)C1=CC=CC=C1, Reagents are:m6:O;m1_m2_m3_m5:O1CCCC1, and Products are 0:C1(=CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1C2=CC=CC=C2C=2C=CC=CC12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12.3 cm3 (30.7 mmol) of a 2.5 molar hexane solution of n-butyllithium were slowly added to a solution of 5.10 g (30.7 mmol) of fluorene in 60 cm3 of tetrahydrofuran at room temperature. After 40 minutes, 7.07 g (30.7 mmol) of diphenylfulvene were added to the orange solution and the mixture was stirred overnight. 60 cm3 of water were added to the dark red solution, whereupon the solution became yellow in color, and the solution was extracted with ether. The ether phase was dried over MgSO4 and concentrated and the residue was left to crystallize at -35° C. 5.1 g (42%) of 1,1-cyclopentadienyl-(9-fluorenyl)diphenylmethane were obtained as a beige powder. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5_m6:C1=C2C(=CC(=C1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)OC(=O)C=C2;m1_m2_m3_m4_m5_m6:C(C1=CC=CC=C1)Cl;m1_m2_m3_m4_m5_m6:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4_m5_m6:C1COCCOCCOCCOCCOCCO1;m1_m2_m3_m4_m5_m6:[I-].[K+], Reagents are:m1_m2_m3_m4_m5_m6:CN(C=O)C, and Products are 0:C(C1=CC=CC=C1)OC1=C(C=C2C=CC(OC2=C1)=O)OC1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Esculin (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), catalytic amounts of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were placed in an eggplant-shaped flask (100 ml). The mixture was reacted while stirred at 60° C. for 8 hours. The reaction mixture was concentrated under reduced pressure and the residue was poured into ice water. The precipitated crystals were filtered out and recrystallized from methanol to obtain 7-benzyloxy-6-D-glucopyranosyloxycoumarin (VIII-2) (melting point=184° to 186° C., mass spectrum (M+)=430, yield=86.4%). |
Here is a chemical reaction formula: Reactants are:m1_m2:N1C=NC=C1;m1_m2:COP(=O)(C(=C)S(=O)(=O)OC)OC;m3:Br[Si](C)(C)C;m4:O, Reagents are:m5:C(Cl)(Cl)Cl, and Products are 0:N1(C=NC=C1)CC(S(=O)(=O)O)P(=O)(O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.68 g (0.01 mole) of imidazole and 2.30 g (0.01 mole) of methyl 1-dimethoxyphosphinylethenesulfonate (U.S. Pat. No. 5,011,938 issued to Barnett et al. on Apr. 30, 1991) in 20 ml of chloroform is stirred at 20°-50° for one day. The reaction is cooled to room temperature, and 10.7 g (0.07 mole) of bromotrimethylsilane is added. The mixture is stirred at 20°-30° for 2-3 days, and to it is then added 20 ml water. The mixture is stirred for about 30 minutes, and the layers are separated. The water layer is extracted several times with CHCl3 (extracts are discarded) and is evaporated to dryness under vacuum. The residue is triturated with acetone to give a solid, which is collected by filtration and recrystallized from water/acetone to afford 2-(1-imidazolyl)-1-phosphonoethanesulfonic acid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:P(=O)(O)(O)C(CNC=1C=NC=CC1)S(=O)(=O)O, Reagents are:m1_m2_m3:[Pd];m1_m2_m3:O, and Products are 0:P(=O)(O)(O)C(CNC1CNCCC1)S(=O)(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1 g of 1-phosphono-2-(3-pyridinylamino)ethanesulfonic acid and 0.5 g of palladium on charcoal catalyst in 50 ml of distilled water is hydrogenated on a Parr apparatus at 40 PSI for about 2 days. The catalyst is removed by filtration, and the filtrate is concentrated to a few mls. Ethanol is added slowly to precipitate a solid, which is recrystallized from water/ethanol to afford 1-phosphono-2-(3-piperidinylamino)ethanesulfonic acid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:P(=O)(O)(O)C(CC1=NC=CC=C1)S(=O)(=O)O, Reagents are:m1_m2_m3:[Pd];m1_m2_m3:O, and Products are 0:P(=O)(O)(O)C(CC1NCCCC1)S(=O)(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1 g of 1-phosphono-2-(2-pyridinyl)ethanesulfonic acid and 0.5 g of palladium on charcoal catalyst in 50 ml of distilled water is hydrogenated on a Parr apparatus at 40 PSI for about 2 days. The catalyst is removed by filtration, and the filtrate is concentrated to a few mls. Ethanol is added slowly to precipitate a solid, which is recrystallized from water/ethanol to afford 1-phosphono-2-(2-piperidinyl)ethanesulfonic acid. |
Here is a chemical reaction formula: Reactants are:m4_m7:O;m3_m6:C(C=C)#N;m2:C(CCC)[Li];m1_m5:[Li+].C(C)OP(=O)(OCC)CS(=O)(=O)[O-], Reagents are:m4_m7:C(C)(=O)O;m3_m6:C1CCOC1;m1_m5:O1CCCC1, and Products are 0:[Li+].C(#N)CCC(S(=O)(=O)[O-])P(=O)(OCC)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 2.38 g (0.01 mole) of diethoxyphosphinylmethanesulfonate lithium salt (Carretero, et al.; Tetrahedron, 43, 5125 (1987)) in 50 ml of anhydrous tetrahydrofuran is stirred in a -40° bath under a dry nitrogen atmosphere. To this is added n-butyl lithium (4.4 ml of 2.5M solution in hexanes; 0.011 mole) via syringe over 5 minutes. The reaction mixture is allowed to warm to -15° and is stirred at this temperature for about one hour. To it is then added rapidly a solution of 0.53 g (0.01 mole) of acrylonitrile in 3 ml of anhydrous THF. The reaction mixture is stirred for 1 hour at -15° , and is then allowed to warm to room temperature over several hours as the bath warms up. It is stirred at ambient temperature for several hours, and then is quenched by addition of 50 ml of water containing 0.6 g (0.01 mole) of acetic acid. The reaction mixture is concentrated under vacuum on a rotary evaporator to get rid of the THF, and the aqueous layer is extracted with ether to remove some impurities. The water layer is evaporated to dryness under vacuum, and the resulting residue is purified by flash chromatography on silica gel using chloroform/methanol as eluant, to afford 3-cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:[H-].[Na+];m1_m5_m2:N1C(NCC1)=O;m3:BrCC1=CC=C(C#N)C=C1;m4:O, Reagents are:m1_m5_m2:CN(C=O)C, and Products are 0:O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was ritered to give 4,4'-[(2-oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m2_m3_m4:BrCC=1C=C(C#N)C=CC1;m1_m2_m3_m4:[H-].[Na+], Reagents are:m1_m2_m3_m4:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 1 above, 2,3-dihydro4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chromatography on silica; NMR (DMSO-d6) 11.02 (s,1), 7.4 (m,4), 7.3 (m,2), 7.2 (m,7), 4.75 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m3_m7:BrCC=1C=C(C(=O)OC)C=CC1;m1_m5_m2_m6:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m5_m2_m6:[H-].[Na+], Reagents are:m3_m7:CN(C)C=O;m1_m5_m2_m6:CN(C)C=O;m1_m5_m2_m6:CN(C)C=O, and Products are 0:COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DMF was then added and the reaction stirred for 10 min at 50° C. The mixture was poured into 1N HCl, filtered, washed with water and dried. Chromatography on silica gel (2% EtOH in 7:3 methylene chloride/ethyl acetate) afforded 1.2 g of 3-(3-methoxycarbonylphenyl)methyl-4,5-diphenyl-1H-imidazol-2-one as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:BrCC1=CC=C2C=CC(=CC2=C1)C#N;m1:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), 7.9 (d,1), 7.85 (d,1), 7.55 (m,3), 7.4 (m,2), 7.2 (m,9), 7.0 (m,3), 5.1 (s,2), 4.95 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2;m2:Cl, Reagents are:m1_m3:CO, and Products are 0:SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Combine 2-[4-(2-Benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid, tert-butyl ester (0.229 mmol) in degassed methanol (3 mL) and cool in an ice bath. Treat with degassed 1N aqueous lithium hydroxide (1.0 mL) and stir, allowing the ice bath to warm gradually over 3 hours. With the reaction at 0° C., acidify with 5% hydrochloric acid. Partition between methylene chloride and water, dry (Na2SO4) and purify by silica gel chromatography to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m5:C(CC=1C(C(=O)O)=CC=CC1)(=O)O;m2_m6:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4:[OH-].[Na+];m3:O, Reagents are:m1_m5:O1CCCC1;m2_m6:O1CCCC1, and Products are 0:OCC1=C(C=CC=C1)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve homophthalic acid (22.2 g, 0.123 mmol) in tetrahydrofuran (250 mL) and add dropwise at room temperature to a slurry of lithium aluminum hydride (15.5 g, 0.407 mol) in tetrahydrofuran (500 mL). Heat at reflux for 18 hours, cool in an ice bath and carefully add, by dropwise addition, water (16 mL), followed by 50% sodium hydroxide (16 mL). Remove the ice bath, add water slowly with stirring and stir until the gray precipitate turns white and evolution of gas ceases. Filter, wash solids with methylene chloride, dry (MgSO4) and evaporate the solvent in vacuo to give 2-(2-hydroxymethyl-phenyl)-ethanol as a viscous oil (18.4 g, 98%). |
Here is a chemical reaction formula: Reactants are:m4:S(=O)(=O)(C)Cl;m3_m5:[Cl-].[Li+];m1_m2:OCC1=C(C=CC=C1)CCO;m1_m2:N1=C(C=C(C=C1C)C)C, Reagents are:m3_m5:CN(C=O)C, and Products are 0:ClCC1=C(C=CC=C1)CCOS(=O)(=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Mix 2-(2-hydroxymethyl-phenyl)-ethanol (12.0 g, 78.8 mmol) and collidine (23 mL, 0.17 mol) and treat with lithium chloride (7.35 g, 0.173 mmol) in dimethylformamide (125 mL). Cool in an ice bath and treat, by dropwise addition, with mesyl chloride (13.4 mL). Stir at 0° C. for 4 hours, partition between ice water (300 mL) and a 1:1 mixture of ether:pentane (2×400 mL). Wash the organic layer with a saturated solution of CuSO4 (2×200 mL), dry (MgSO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate) to give the title compound as a pale yellow oil (8.8 g, 45%). |
Here is a chemical reaction formula: Reactants are:m1_m3:ClCC1=C(C=CC=C1)CCOS(=O)(=O)C;m2:CC(C)([O-])C.[K+], Reagents are:m1_m3:CCOCC, and Products are 0:ClCC1=C(C=CC=C1)C=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester (8.8 g, 35.4 mmol) in ether (80 mL) and cool to -35° C. Add potassium t-butoxide (10 g, 89 mmol) and stir for 30 minutes. Add water (50 mL) and ether (150 mL), extract, dry (Na2SO4) and purify by silica gel chromatography (2:3 methylene chloride/pentane) to give 1-chloromethyl-2-vinyl-benzene as a colorless oil (4.43 g, 82%). |
Here is a chemical reaction formula: Reactants are:m1_m4:ClCC1=C(C=CC=C1)C=C;m2:[I-].[Na+];m3:O, Reagents are:m1_m4:CC(=O)C, and Products are 0:ICC1=C(C=CC=C1)C=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 1-chloromethyl-2-vinyl-benzene (4.0 g, 26 mmol) in acetone (100 mL) and add sodium iodide (4.5 g, 30 mmol). Heat at gentle reflux for 30 minutes. Cool, add water (150 mL) and extract with pentane (200 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (95%). |
Here is a chemical reaction formula: Reactants are:m2_m3:C(CCC)[Li];m2_m3:CCCCCC;m5:ICC1=C(C=CC=C1)C=C;m1_m6:CSC(=NCC(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)SC;m4:CN(C)P(=O)(N(C)C)N(C)C, Reagents are:m1_m6:O1CCCC1;m7:O1CCCC1, and Products are 0:CSC(=NC(C(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)CC3=C(C=CC=C3)C=C)SC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-(bis-methylsulfanyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone (7.91 g, 21.0 mmol) in tetrahydrofuran (100 mL) and cool to -78° C. Treat, by dropwise addition, with 1.6M n-butyllithium in hexane (13.1 mL, 21 mmol). Stir for 1.5 hours, then add hexamethylphosphotriamide (HMPA) (4.25 mL, 24.4 mmol). Stir for 15 minutes and add, via cannula, a solution of 1-iodomethyl-2-vinyl-benzene (6.1 g, 25 mmol) in tetrahydrofuran (100 mL). Stir overnight at room temperature, partition between saturated ammonium chloride (2×75 mL) and ethyl acetate (400 mL). Dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a white solid (4.5 g). |
Here is a chemical reaction formula: Reactants are:m1_m4:NC(C(=O)O)CC1=C(C=CC=C1)C=C;m2_m3:C([O-])([O-])=O.[Na+].[Na+];m2_m3:C(=O)(OCC)N1C(C=2C(C1=O)=CC=CC2)=O, Reagents are:m1_m4:O, and Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)O)CC1=C(C=CC=C1)C=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-amino-3-(2-vinyl-phenyl)-propionic acid (3.40 g) in water (75 mL) and add sodium carbonate (1.97 g, 18.6 mmol) and N-carbethoxyphthalimide (2.81 g, 12.8 mmol). Stir for 2.5 hours, wash with methylene chloride (200 mL), acidify to pH 1 with cold concentrated hydrochloric acid and extract with ethyl acetate (3×200 mL), dry (Na2SO4), evaporate the solvent in vacuo and purify by silica gel chromatography (1:1:2% hexane/ethyl acetate/acetic acid) followed by recrystallization (isopropranol) to give the title compound as a pale yellow solid (2.47 g). |
Here is a chemical reaction formula: Reactants are:m2_m3:N1=CC=CC=C1;m2_m3:C[Si](CCO)(C)C;m4:Cl.CN(CCCN=C=NCC)C;m1_m5:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)O)CC1=C(C=CC=C1)C=C, Reagents are:m6:C(C)(=O)OCC;m1_m5:O1CCCC1, and Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid (2.47 g, 7.69 mmol) in tetrahydrofuran (35 mL) and cool in an ice bath. Treat with pyridine (1.6 mL, 20 mmol) and 2-(trimethylsilyl)ethanol (2.3 mL, 16 mmol). Stir for 30 minutes and add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (2.21 g, 11.5 mmol). Stir for 22 hours at 5° C., then at room temperature for 1.5 hours. Cool to 0° C., add 0.6 times all reagents and stir at room temperature overnight. Dilute with ethyl acetate (150 mL), wash with 5% sulfuric acid (40 mL) and saturated sodium hydrogen carbonate (40 mL). Back extract with methylene chloride (100 mL), wash with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give the title compound (2.61 g, 81%). |
Here is a chemical reaction formula: Reactants are:m2:O=[O+][O-];m1_m3_m4:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C, Reagents are:m1_m3_m4:C(Cl)Cl;m1_m3_m4:CO, and Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (2.61 g, 6.19 mmol) in methylene chloride (70 mL) and methanol (75 mL). Cool to -78° C. and treat with ozone until a blue color persists. Purge with nitrogen and add dimethylsulfide (7 mL) and pyridine (0.35 mL). Allow to warm to room temperature gradually overnight. Partition between methylene chloride (100 mL) and water (40 mL). Extract the aqueous with methylene chloride (50 mL), dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a colorless viscous oil (2.65 g, 100%). |
Here is a chemical reaction formula: Reactants are:m2:C1(=CC=CC=C1)OC;m3:FC(C(=O)O)(F)F;m1_m4:C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid, tert-butyl ester (141 mg, 0.229 mmol) in methylene chloride (5 mL) and treat with anisole (0.12 mL, 1.15 mmol) then with trifluoroacetic acid (1.5M). Stir at room temperature for 15 hours, partition between ethyl acetate (25 mL) and brine (15 mL). Wash the organic layer with brine (15 mL), dry (Na2SO4) and purify by silica gel chromatography (1:1 hexane/ethyl acetate followed by 1:1:0.01 hexane/ethyl acetate/acetic acid) to give the title compound as a white solid (157 mg). |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2;m2:Cl, Reagents are:m1_m3:CO, and Products are 0:SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid (0.229 mmol) in degassed methanol (3 mL) and cool in an ice bath. Treat with degassed 1N aqueous lithium hydroxide (1.0 mL) and stir, allowing the ice bath to warm gradually over 3 hours. With the reaction at 0° C., acidify with 5% hydrochloric acid. Partition between methylene chloride (75 mL) and water (25 mL), dry (Na2SO4) and purify by silica gel chromatography (3:1:0.01 hexane/ethyl acetate/acetic acid followed by 1:1:0.01 hexane/ethyl acetate/acetic acid to give the title compound as a white solid (84 mg, 80.8%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m8_m9:[H-].[Na+];m1_m2_m8_m9:C(C)(C)(C)OC(=O)NCC\C=C\C=1C=NC=NC1;m3:C(C)(C)NC(C)C;m4_m5:IC, Reagents are:m7:O;m6:O;m1_m2_m8_m9:COCCOC;m1_m2_m8_m9:CN(C)C=O;m4_m5:COCCOC, and Products are 0:CN(CC\C=C\C=1C=NC=NC1)C(=O)OC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2 SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil, The oil was chromatographed on silica gel (50 g), eluting with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:BrC(Br)(Br)Br;m1_m2_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m3:N1=CC(=CC=C1)C=O, Reagents are:m1_m2_m4:C(Cl)Cl, and Products are 0:BrC(=CC=1C=NC=CC1)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at ambient temperature. The reaction mixture was extracted with aqueous 6N hydrochloric acid (3×25 mL), the aqueous layer basified with solid sodium bicarbonate to pH 8-9 and extracted with chloroform (4×25 mL). The combined organic liquours were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give a dark colored syrup. The crude product was chromatographed on silica gel (70-230 mesh) with chloroform:methanol (95:5) as eluant, to afford a light yellow solid (5.0 g, 70%) which rapidly turned dark on standing. |