| 93% |
|
Acetonitrile (4.02 g, 97.8 mmol) was added to a THF (50 mL) suspension of sodium hydride (3.91 g, 97.8 mmol), followed by heating at 70C for 1 minute. The reaction liquid was cooled to room temperature and a THF (20 mL) solution of <strong>[2557-13-3]methyl 3-(trifluoromethyl)benzoate</strong> (10.0 g, 48.9 mmol) was added dropwise thereto, followed by heating under stirring at 60C for 6 hours. After completion of the reaction, solvent was removed by evaporation and the resulting residue was poured into water, followed by extraction with ethyl acetate. After the resulting extract solution was washed with water and brine, the solvent was removed by evaporation. The resulting residue was purified on a silica gel column (Kiesel gel 60 manufactured by MERCK, 30% AcOEt-Hex) to obtain 3-oxo-3-[3-(trifluoromethyl)phenyl]propionitrile (9.67 g, 93%). Alternatively, the compound can be also produced by the following method. Sodium hydride (3.56 g, 89.0 mmol) was added to a toluene (60 mL) solution of <strong>[2557-13-3]methyl 3-(trifluoromethyl)benzoate</strong> (9.08 g, 44.5 mmol), followed by heating under stirring to 85C. While the gas generation state was taken into account, acetonitrile (3.65 g, 89.0 mmol) was slowly added dropwise thereto, followed by continuation of heating under stirring at 85C for 2 hours. After completion of the reaction, the reaction liquid was poured into water, followed by extraction with toluene. Thereafter, the resulting aqueous layer was cooled with ice water and acidified with concentrated hydrochloric acid. After filtration of precipitated crystals, the resulting crystals were washed with water and hexane and dried to obtain 3-oxo-3-[3-(trifluoromethyl)phenyl] propionitrile (8.17 g, 80%). 1H-NMR (400MHz, CDCl3): 4.14(s, 2H), 7.71(t, 1H, J=8.0Hz), 7.93(d, 1H, J=8.0Hz), 8.12(d, 1H, J=8.0Hz), 8.18(s, 1H). mp: 63C |
| 80% |
|
Acetonitrile (4.02 g, 97.8 mmol) was added to a THF (50 mL) suspension of sodium hydride (3.91 g, 97.8 mmol), followed by heating at 70C for 1 minute. The reaction liquid was cooled to room temperature and a THF (20 mL) solution of <strong>[2557-13-3]methyl 3-(trifluoromethyl)benzoate</strong> (10.0 g, 48.9 mmol) was added dropwise thereto, followed by heating under stirring at 60C for 6 hours. After completion of the reaction, solvent was removed by evaporation and the resulting residue was poured into water, followed by extraction with ethyl acetate. After the resulting extract solution was washed with water and brine, the solvent was removed by evaporation. The resulting residue was purified on a silica gel column (Kiesel gel 60 manufactured by MERCK, 30% AcOEt-Hex) to obtain 3-oxo-3-[3-(trifluoromethyl)phenyl]propionitrile (9.67 g, 93%). Alternatively, the compound can be also produced by the following method. Sodium hydride (3.56 g, 89.0 mmol) was added to a toluene (60 mL) solution of <strong>[2557-13-3]methyl 3-(trifluoromethyl)benzoate</strong> (9.08 g, 44.5 mmol), followed by heating under stirring to 85C. While the gas generation state was taken into account, acetonitrile (3.65 g, 89.0 mmol) was slowly added dropwise thereto, followed by continuation of heating under stirring at 85C for 2 hours. After completion of the reaction, the reaction liquid was poured into water, followed by extraction with toluene. Thereafter, the resulting aqueous layer was cooled with ice water and acidified with concentrated hydrochloric acid. After filtration of precipitated crystals, the resulting crystals were washed with water and hexane and dried to obtain 3-oxo-3-[3-(trifluoromethyl)phenyl] propionitrile (8.17 g, 80%). 1H-NMR (400MHz, CDCl3): 4.14(s, 2H), 7.71(t, 1H, J=8.0Hz), 7.93(d, 1H, J=8.0Hz), 8.12(d, 1H, J=8.0Hz), 8.18(s, 1H). mp: 63C |
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