5-phenylpyridine-2-carboxylic Acid → (5-Phenylpyridin-2-yl)methanol

Participants

Reaction Steps

To a solution of 3-phenyl-6-carboxypyridine (1.05 g, 5.27 mmol) in tetrahydrofuran (25 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (10.0 mL, 10.0 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 6 hours, cooled to 0° C., and quenched by dropwise addition of water (0.50 mL), 4N aq. NaOH (0.50 mL), and water (1.5 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, 0-5% MeOH in CH2Cl2) to afford the title compound.

Provenance & Evidence