Dimethyl Sulfoxide → HCID 12080541, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (12 mL, 24 mmol) was added to CH2Cl2 (250 mL) at −78° C. DMSO (3.75 g, 48 mmol) was added dropwise to the mixture and stirring was continued for 15 min. A solution of alcohol 20 (2.57 g, 12 mmol) in CH2Cl2 (20mL) was then added dropwise. After 1 hr at −78° C., Et3N (9.72 g, 96 mmol) was added and the mixture was warmed to 23° C. After 1 h, the mixture was poured into NaHCO3 (sat) and the organic layer was seperated. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layer was washed with brine, dried (Na2SO4), concentrated and purified by FCC (silica gel, 100% hexane; 2:1, hexane/CH2Cl2) to afford the above named aldehyde 21.

Provenance & Evidence