Dimethyl Sulfoxide → HCID 86666718, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added CH2Cl2 and oxalyl chloride (1.21 mL, 13.8 mmol) before the solution was cooled to −78° C. To this solution was added DMSO (1.47 mL, 20.65 mmol) and the solution stirred for 15 min before addition of (4-chlorophenyl)(2-(3-(hydroxymethyl)-5-methylisoxazol-4-yl)phenyl)methanol (1.14 g, 3.44 mmol) dissolved in CH2Cl2. The reaction was stirred for 15 min at −78° C. before addition of Et3N (3.84 mL, 27.5 mmol) and warming the reaction to room temperature overnight. This reaction was diluted with water 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)-5-methylisoxazole-3-carbaldehyde (1.10 g, 3.38 mmol). LC/MS m/z 326 [M+H]+.

Provenance & Evidence