Water → 4,4-dimethyl-3,4-dihydro-1H-isochromen-6-ol

Participants

Reaction Conditions

Reaction Steps

6-methoxy-4,4-dimethyl-3,4-dihydro-1H-isochromene (Intermediate 41, 350 mg, 1.8205 mmol) was dissolved in DCM (10 mL) and the solution was cooled to 0° C. Tribromoborane (228.04 mg, 0.9102 mmol) was added and the resulting mixture was stirred at 0° C. for 2 hours. Water (10 mL) was added and the two phases were separated. Organics were dried over Na2SO4, filtered and dried in vacuo. The crude was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent affording the title compound (42 mg).

Provenance & Evidence