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

Participants

Reaction Steps

To a stirred suspension of 50% sodium hydride in oil (13.89 g) in dimethoxyethane (100 ml) at -2° C., was added dropwise over 90 minutes, a mixture of ethyl β-(N-n-butyl-2-oxo-4-pyridyl)propionate (58.19 g) and ethyl formate (25.73 g), the reaction temperature being maintained below 5° C. The reaction mixture was then allowed to warm to room temperature overnight, poured on to ice and extracted successively into petroleum ether (40°-60°) (150 ml) and diethyl ether (3×100 ml). The combined organic extracts were washed with water (40 ml); and the aqueous layer and aqueous washings were taken to pH 5 with glacial acetic acid. A brown oil came out of solution which was extracted into ethyl acetate (3×150 ml). The combined ethyl acetate extracts were washed with water (2×30 ml), dried over MgSO4 and evaporated under reduced pressure. The residue was washed with petroleum ether (40°-60°) and dried in vacuo to afford as a pale brown solid, ethyl α-formyl-β-(N-n-butyl-2-oxo-4-pyridyl)propionate (54.84 g).

Provenance & Evidence