3-Fluoropyridine-4-carboxylic acid → (3-Fluoropyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

At 0° C. LAH (200 mg, 4 eq.) was added to 3-fluoro-isonicotinic acid (186 mg, 1.32 mmol, 1 eq.) suspension in 25 mL THF. The reaction was stirred at 0° C. for 1 hour. The reaction was quenched by adding 0.2 mL water, followed by 0.4 mL 10% NaOH aqueous solution and 0.6 mL water at 0° C. Ethyl acetate was added to the reaction crude and washed with brine. n-Butanol was used to extract back from the brine. The organic layers were combined and concentrated down and purified (silica gel, 0-15% MeOH/DCM) to give colorless oil (78 mg, 46%). 1H NMR (300 MHz, CD3OD): δ 8.39 (m, 2H), 7.61 (m, 1H), 4.86 (s, 2H).

Provenance & Evidence