Hydrochloric Acid → (2-Chloro-6-methylpyridin-4-yl)methanol

Participants

Reaction Steps

Borane-THF complex (16.5 mL, 1.06 M solution in THF) was added to a solution of 2-chloro-6-methylpyridine-4-carboxylic acid (2 g) in THF (10 mL), and the mixture was heated under reflux for 12 hours. 5 M hydrochloric acid was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was neutralized by adding a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%) to give the title compound (1.75 g).

Provenance & Evidence