Sodium hydride → 2-[2-chloro-4-(pyrrolidine-1-carbonyl)benzyl]-3-oxopentanoic Acid Ethyl Ester

Participants

Reaction Conditions

Reaction Steps

A solution of 3-oxopentanoic acid ethyl ester (14 mL) in 1,2-dimethoxyethane (25 mL) was added to a stirred suspension of sodium hydride (60% in oil, 3.7 g) in 1,2-dimethoxyethane (250 mL) and N,N-dimethylformamide (30 mL) at 0° C. and the resulting mixture was stirred at 0° C. for 10 minutes. A solution of (4-bromomethyl-3-chlorophenyl)pyrrolidin-1-ylmethanone (9.7 g) in 1,2-dimethoxyethane (25 mL) was added and the resulting mixture warmed to room temperature and then stirred at this temperature for 20 hours. The mixture was diluted with saturated aqueous ammonium chloride solution, extracted with diethyl ether and the combined extracts washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (9:1 by volume) to afford title compound, 1.8 g.

Provenance & Evidence