m-Chloroperbenzoic acid → (3R)-3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

Participants

Reaction Steps

A solution of 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one (1.7 g, 9.0 mmol) in DCM (60 mL) was treated with m-CPBA (3.1 g, 18 mmol) and then stirred overnight at room temperature. The reaction was then diluted with water (50 mL) and DCM (50 mL). The organic layer was further washed successively with saturated aqueous sodium bicarbonate (30 mL), water (30 mL), and brine (30 mL). The organic layer was then dried over magnesium sulfate, filtered and concentrated. The residue was purified via MPLC (15-40% EtOAc/Hex) to give (3R)-3-methyl-6-(oxiran-2-yl)isochroman-1-one.

Provenance & Evidence