Diethyl Carbonate → Diethyl 3,4-difluorophenylmalonate

Participants

Reaction Steps

A mixture of ethyl (3,4-difluorophenyl)acetate (11.3 g) in THF (50 ml) was added to a mixture of sodium hydride (60%, 4.74 g), diethyl carbonate (34.2 mL) and THF (250 mL) at room temperature, and the mixture was heated under reflux for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.8 g).

Provenance & Evidence