Aluminium lithium hydride → {6-[2-(Trifluoromethyl)phenyl]pyridin-3-yl}methanol

Participants

Reaction Steps

To a solution of 2-(2-Trifluoromethylphenyl)-5-carboxypyridine (220 mg, 1.23 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (1.23 mL, 1.23 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 16 hours, cooled to 0° C., and quenched by dropwise addition of water (0.05 mL), 2.5N aq. NaOH (0.05 mL), and water (0.15 mL). Sodium sulfate was added, the reaction filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, CH2Cl2 then EtOAc) to afford the title compound.

Provenance & Evidence