Acetone → 5-(2,3-dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one (see step A for 1-3), (2.00 g, 10.6 mmol) in acetone (30 mL) and water (10 mL) was added OsO4 (0.27 g, 1.06 mmol) and NMO (6.70 g, 11.7 mmol), the solution was stirred at 25° C. for 18 h. The reaction mixture was diluted with water (30 mL) and the aqueous layer was extracted with CH2Cl2 (3×40 mL). The organic layers were combined, washed with brine (2×40 mL), dried with MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (0-10% methanol in dichloromethane) to give the title compound.

Provenance & Evidence