Dimethyl Sulfoxide → HCID 86666720, compound

Participants

Reaction Steps

To a round bottomed flask was added CH2Cl2 (15 mL) and oxalyl chloride (0.24 mL, 2.75 mmol). The solution was cooled to −78° C. before addition of DMSO (0.29 mL, 4.13 mmol) and the reaction stirred at −78° C. for 15 minutes before addition of (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone (0.451 mg, 1.38 mmol) dissolved in CH2Cl2 (5 mL). The reaction was stirred an additional 15 min at −78° C. before addition of Et3N (0.959 mL, 6.88 mmol) and removal of the cold bath. After warming to room temperature water was added and the layers separated. The aqueous was extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazole-5-carbaldehyde (0.448 g, 1.38 mmol). LC/MS m/z 326 [M+H]+.

Provenance & Evidence