Methyl morpholine oxide → 5-(1,2-Dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

Participants

Reaction Steps

To (E)-4-methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one (300 mg, 1.59 mmol) in acetonitrile/water (10/1, 18 mL) was added NMO (243 mg, 2.07 mmol) and potassium osmate(VI) dihydrate (29.4 mg, 0.080 mmol) at 0° C. The reaction mixture was allowed to warm to rt and stirred at rt for 2 h. TLC showed the reaction completed. The reaction mixture was filtered through a pad of silica gel, rinsed with 10% MeOH/DCM. The crude product was purified with column chromatography (0-10% MeOH/DCM) to give the title compound. LC/MS: [(M+1)]+=223

Provenance & Evidence