Borane → Methyl 3-tert-butyl-5-(hydroxymethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (8.66 g, 0.0293 mol) in THF (60 mL) was slowly added borane-dimethyl sulfide complex (7.8 mL, 0.088 mol) over 20 min at rt. The reaction mixture was heated at 50° C. for 2 h. An additional amount of borane-dimethyl sulfide complex (7.8 mL, 0.088 mol) was added to reaction mixture and the heat increased to 80° C. The reaction mixture was allowed to stir for an additional 2 h. Unreacted borane was quenched by the addition of MeOH. Water was added and the mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography and triturated to give methyl 3-tert-butyl-5-(hydroxymethyl)benzoate (3.0 g, 46%) as a white solid. LCMS ES+ 223.

Provenance & Evidence