Acetaldehyde → 1-(7-Methoxyfuro[2,3-c]pyridin-2-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

A solution of 7-methoxyfuro[2,3-c]pyridine (1.5 g) in dry tetrahydrofuran (50 ml) was stirred at −78° C. under dry nitrogen. n-Butyllithium (1.6N solution in hexanes, 6.9 ml) was added dropwise and the resulting solution stirred at −78° C. for 60 minutes. Acetaldehyde (5.7 ml) was added and stirring continued at −78° C. for 90 minutes before warming to room temperature. The mixture was diluted with water (100 ml) and extracted with ethyl acetate (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 (1.8 g) as a brown oil.

Provenance & Evidence