Dimethyl Sulfide → HCID 54383053, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 36 (1.38 g, 2.27 mmol) in 65 mL of CH2Cl2 at -78° C. is added m-CPBA (612 mg, 64%, 2.27 mmol). The reaction mixture is allowed to warm to -15° C. and then quenched with dimethyl sulfide (1 mL, 13.6 mmol) and allowed to warm to room temperature. The reaction mixture is diluted with 50 mL of CH2Cl2, extracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL), dried over Na2SO4, filtered, and concentrated to afford a white solid. The sulfoxide is purified using flash chromatography (30% EtOAc/hexane) to afford 1.07 g (76%) of the title compound 37 as a mixture of diastereomers: Rf 0.35 and 0.38 (30% EtOAc/hexane).

Provenance & Evidence