Dimethyl Sulfoxide → HCID 19029385, compound

Participants

Reaction Steps

Oxalyl chloride (3.2 g) in CH2Cl2 (125 mL) was cooled to -78° C. and treated with a solution of DMSO (4.12 g) in CH2Cl2 (20 mL) over 15 minutes. This mixture was stirred for 15 minutes whereupon a CH2Cl2 (30 mL) solution of 3,4-Dichloro-beta-(2-hydroxyethyl)-N-[(3,5-dimethoxyphenyl)methyl]benzenepropanamide (9.0 g) was added dropwise. The mixture was stirred for 30 minutes and then treated with a solution of Et3N (6.4 g) in CH2Cl2 (25 mL) and stirred for an additional 30 minutes at -78° C., then allowed to warm to ambient temperature. The reaction mixture was washed with water (125 mL), the organic fraction separated, dried over MgSO4, filtered and concentrated under reduced pressure to yield an oil (12 g). Silica gel chromatography eluting with 10% EtOAc/CH2Cl2 gave the title compound (8.2 g).

Provenance & Evidence