Triethylamine → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine

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Reaction Steps

A solution of oxalyl chloride (0.97 ml) in dry dichloromethane (10 ml) was stirred at −55° C. under an atmosphere of dry nitrogen. A solution of dimethyl sulfoxide (1.7 ml) in dry dichloromethane (5 ml) was added dropwise and stirring continued for 5 minutes at −55° C. 1-(7-Methoxyfuro[2,3-c]pyridin-2-yl)ethanol (1.9 g) in dimethyl sulfoxide (15 ml) was added dropwise and stirring continued for a further 15 minutes. Triethylamine (6.9 ml) was added and the mixture stirred for a further 5 minutes at −55° C. before warming to room temperature. The mixture was diluted with water (100 ml) and extracted with dichloromethane (3×100 ml). The combined organic extracts were dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 50% hexane in ethyl acetate gave the title compound (1.2 g) as a pale yellow solid.

Provenance & Evidence