反应详情

To 1 g of ethyl cyanoacetate dissolved in 5 mL of N,N-dimethylformamide, 0.5 g of sodium hydride was added under cooling with ice, and after stirring at room temperature for 30 minutes, 1.5 g of ethyl p-fluorophenylcinnamate was added. The reaction mixture was stirred at room temperature for 4 hours. After addition of ethanol under cooling with ice, the reaction mixture was poured into iced water and extracted with a solvent mixture of hexane and ethyl acetate. The extract was washed with water, and dried and concentrated. The resulting oily substance was separated by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 1.8 g of diethyl 2-cyano-3-(p-fluorophenyl)glutarate as a diastereomer mixture.

1. temperatureunder cooling with ice
2. stirringThe reaction mixture was stirred at room temperature for 4 hours
3. temperatureunder cooling with ice
4. extractionextracted with a solvent mixture of hexane and ethyl acetate
5. washThe extract was washed with water
6. customdried
7. concentrationconcentrated
8. customThe resulting oily substance was separated by silica gel column chromatography (hexane:ethyl acetate=9:1)