Diethyl Ether → Imidazo[1,2-a]pyridin-8-ylmethanol

Participants

Reaction Steps

To a cold solution of methyl imidazo[1,2-a]pyridine-8-carboxylate (5.55 g, 31.53 mmol, 1 eq) in THF (100 mL) was added LAH in ether (1 M solution in ether, 4 equiv.) and then stirred at rt for 6 h. The reaction mixture was cooled to 0° C. and quenched with water/15% NaOH/water. Reaction mixture was diluted with ethyl acetate and stirred at room temperature for 15 min and then filtered. The solid was washed with ethanol and the organic layers were combined, dried and evaporated to give the alcohol, which was purified by column chromatography to yield the desired product in 40% yield.

Provenance & Evidence