Ethyl formate → ethyl alpha-formyl-beta-(N-benzyl-2-oxo-4-pyridyl)propionate

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred suspension of 50% sodium hydride in oil (6.37 g) in dimethoxyethane (80 ml) was added dropwise over 25 minutes a mixture of ethyl β-(N-benzyl-2-oxo-4-pyridyl)propionate (30.29 g) and ethylformate (11.80 g), whilst maintaining the reaction temperature between 5°-8° C. The reaction mixture was allowed to warm slowly to room temperature overnight and then was poured on to ice. A brown solution formed which was extracted successively with petroleum ether (40°-60° C.) (60 ml) and diethyl ether (70 ml). The combined organic extracts were washed with water. The combined aqueous layer and aqueous washings were taken to pH 5 with glacial acetic acid. The solution was cooled whereupon a solid appeared which was collected by filtration, washed with water, washed with ethyl acetate and dried in vacuo to yield ethyl α-formyl-β-(N-benzyl-2-oxo-4-pyridyl)propionate (22.52 g), m.p. 140°-143° C.

Provenance & Evidence