Dimethyl Sulfoxide → 4-(2-Chloro-4-methoxyphenyl)-3-methyl-4-oxobutanal

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Reaction Conditions

Reaction Steps

To a 500 mL, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added DMSO (17.0 mL, 239 mmol) and CH2Cl2 (200 mL). The solution was cooled to −68° C. with a dry ice/acetone bath. To this solution was added oxalyl chloride (10.4 mL, 119 mmol) slowly. The mixture was stirred at −68° C. for 15 min followed by the addition of a solution of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one (12.9 g, 53.0 mmol) in CH2Cl2 (20.0 mL) slowly. After stirring at <−68° C. for 1 h, to the mixture was added Et3N (70.0 mL, 502 mmol). The cooling bath was removed after 5 min and the mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water (200 mL). The aqueous layer was extracted with CH2Cl2 (2×). The combined organic solutions was concentrated in vacuo to dryness and the residue was subjected to column chromatography (silica gel, 1/10 EtOAc/heptane) to give 8.07 g (63%) of light yellow oil as the title compound:

Provenance & Evidence