(2-氨基-5-氯苯基)-环丙基甲酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: (2-Amino-5-chlorophenyl)(cyclopropyl)methanone (450 mg, 2.30 mmol) was dissolved in THF (5 mL), and while stirring the reaction solution at 0° C., vinyl magnesium bromide (1.0 M THF solution, 5.7 mL) was added dropwise thereto. The reaction solution was stirred overnight at room temperature, and then, a saturated aqueous ammonium chloride solution was added to the solution. After the solution was diluted with ethyl acetate, the organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was dissolved in THF (5 mL), and 1,1-carbonyldiimidazole (CDI) (745 mg) was added thereto at room temperature. The reaction solution was stirred at room temperature for 2 hours, followed by ice-cooling, and water was added to the reaction solution. The solution was diluted with ethyl acetate and a saturated aqueous ammonium chloride solution was added thereto. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2), whereby 6-chloro-4-cyclopropyl-4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (610 mg) was quantitatively obtained as a pale white solid. The reaction solution was stirred overnight at room temperature the organic layer was separated washed with saturated brine dried over magnesium sulfate After the drying agent was removed by filtration the solvent was evaporated under reduced pressure The resulting residue was dissolved in THF (5 mL) 1,1-carbonyldiimidazole (CDI) (745 mg) was added at room temperature The reaction solution was stirred at room temperature for 2 hours cooling water was added to the reaction solution The solution was diluted with ethyl acetate a saturated aqueous ammonium chloride solution was added The organic layer was separated washed with saturated brine dried over magnesium sulfate After the drying agent was removed by filtration the solvent was evaporated under reduced pressure The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2), whereby 6-chloro-4-cyclopropyl-4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (610 mg) was quantitatively obtained as a pale white solid

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Amino-5-chlorobenzonitrile (500 mg, 3.28 mmol) was dissolved in THF (10 mL), and while stirring the reaction solution at 0° C., cyclopropyl magnesium bromide (0.5 M THF solution, 26.4 mL) was added dropwise thereto. The reaction solution was stirred overnight under heating at 80° C., followed by ice-cooling, and 2 N hydrochloric acid was added thereto under ice-cooling. After the reaction solution was stirred at room temperature for 2 hours, the solution was diluted with ethyl acetate and then neutralized with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1), whereby (2-amino-5-chlorophenyl)(cyclopropyl)methanone (453 mg, 83%) was obtained as a yellow solid. The reaction solution was stirred overnight under heating at 80° C. cooling under ice-cooling After the reaction solution was stirred at room temperature for 2 hours The organic layer was separated washed with saturated brine dried over magnesium sulfate After the drying agent was removed by filtration the solvent was evaporated under reduced pressure The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/1)