Water → HCID 91507228, compound

Participants

Reaction Steps

Boron trifluoride ether complex (1.83 ml, 14.86 mmol) was added dropwise to a suspension of sodium borohydride (422 mg, 11.14 mmol) in tetrahydrofuran (30 ml) with stirring under ice cooling in 10 min. To this reaction mixture was added a solution of (±)-2-phenyl-1,4-benzoxazin-3-one-8-carboxylic acid (500 mg, 1.86 mmol) in tetrahydrofuran (6 ml) and the mixture was stirred at the same temperature for 5 min. and then at room temperature for 1.5 hrs. The reaction mixture was cooled with ice and water (20 ml) was added dropwise thereto. The mixture was neutralized with saturated sodium bicarbonate solution and then extracted with ethyl acetate. The extract was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure to give (±)-2-phenyl-1,4-benzoxazine-8-methanol (397 mg, 89%) as a pale orange oil.

Provenance & Evidence