Ethyl formate → Ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionate

Participants

Reaction Steps

A mixture of ethyl 3-(6-methoxy-3-pyridyl)propionate (32.74 g), and ethyl formate (17.22 g), was added dropwise over 1.5 hours to a stirred suspension of sodium hydride in oil (50%, 9.38 g), in 1,2-dimethoxyethane (50 ml) cooled to -2°, allowed to stand overnight at room temperature and then poured on to ice. The mixture was extracted with ether and the aqueous phase was adjusted to pH 5 with 2 N sulphuric acid. An oil was precipitated and crystallised on standing to give ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionate (25.9 g, 70%), m.p. 91.5°-94°. A sample recrystallised from aqueous ethanol had m.p. 93°-4°.

Provenance & Evidence