Dimethyl Sulfoxide → HCID 15132295, compound

Participants

Reaction Steps

A mixture of dimethyl sulfoxide (0.5 ml) and dichloromethane (5 ml) was added dropwise to a solution of oxalyl chloride (0.36 ml, 4.18 mmol) in dichloromethane (5 ml) at -78° under argon. After 5 minutes, a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (Compound 25, 1.01 g, 2.98 mmol) in dichloromethane (5 ml), followed by triethylamine (1.66 ml, 11.9 mmol) after 20 minutes, was added. Stirring was continued for 3 hours while the cooling bath attained room temperature. The mixture was quenched with water and extracted with dichloromethane. The dried (magnesium sulfate) extracts on evaporation gave a residue which was purified by a silica column using 2.5% ethyl ether/hexane. Fractions with Rf of about 0.27 (5% ethyl ether/hexane) on evaporation gave the titled ketone as an off-white solid.

Provenance & Evidence