Dimethyl Sulfoxide → HCID 60026693, compound

Participants

Reaction Steps

To a solution of 1.57 mL of oxalyl chloride in 15 mL of dichloromethane at −60° C. was added a solution of 2.55 mL of DMSO in 5 mL of dichloromethane. After 10 minutes, a solution of 3-(2-benzyloxy-5-methylsulfanylphenyl)-3-methylbutan-1-ol (2.84 g, 8.9 mmol) in 5 mL of dichloromethane was added (solids quickly precipitated), followed 15 minutes later by 7.5 mL triethylamine and the reaction mixture became very thick with solids. The reaction mixture was then warmed to room temperature and monitored by TLC. After 1 hour, TLC of an aliquot showed reaction was complete, so water was added to the reaction mixture and the resulting layers were separated. The aqueous layer was washed with dichloromethane and the organics were combined, washed four times with water, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford a yellow oil. The residue was purified on SiO2 (0% to 10% ethyl acetate-hexanes) to give 2.2 g (78.7% yield) of 3-(2-benzyloxy-5-methylsulfanylphenyl)-3-methylbutyraldehyde as a colorless oil that slowly crystallized upon standing.

Provenance & Evidence