Dimethyl Sulfoxide → HCID 67814253, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added DCM (4 mL) and oxalyl chloride (28.0 μl, 0.320 mmol) before the solution was cooled to −78° C. To this solution was added DMSO (37.9 μl, 0.533 mmol) and the reaction stirred at −78° C. for 15 min before addition of (4-chlorophenyl)(2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)phenyl)methanol (120 mg, 0.267 mmol) dissolved in DCM. The solution was stirred for an additional 15 min before addition of Et3N (112 μl, 0.800 mmol) and the reaction warmed to room temperature. Water was added and the layers separated. The aqueous was extracted with DCM and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-chlorophenyl)(2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)phenyl)methanone. LC/MS m/z 448 [M+H]+.

Provenance & Evidence