Benzoic Acid → [3-(Pyridin-3-yl)phenyl]methanol

Participants

Reaction Steps

To a 100 mL recovery flask was added 3-(3-pyridyl)-benzoic acid 45 (2.00 g, 10.0 mmol, 1.0 eq.) and THF (20 mL). The resulting suspension is stirred. BH3 (1.0 M in THF, 15 mL, 15 mmol, 1.5 eq.) was added the resulting mixture was refluxed overnight. Incomplete reduction was observed by LC/MS. Additional BH3 (10 mL) was added and the mixture was refluxed for an additional 6 h. LC/MS indicates complete reduction of the benzoic acid. The reaction mixture was concentrated and diluted with EtOAc. The organic layer was washed with a succession of water, HCl, brine. The combined aqueous layers were extracted with EtOAc. The organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a clear oil. The crude material was purified via flash chromatography (40% to 60% EtOAc/Hex) to give a white solid (995 mg, 53%).

Provenance & Evidence