Dimethyl Sulfoxide → HCID 86586557, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (50 mL, 0.10 mmol) was added to CH2Cl2 (150 mL) at 23° C. and was cooled to −78° C. DMSO (16 g, 0.20 mmol) was added dropwise to the mixture and stirring was continued for 15 min. A solution of alcohol 4 (7.9 g, 0.041 mmol) in CH2Cl2 (50 mL) was then added dropwise, after which Et3N (44 g, 0.44 mmol) was added and the mixture was warmed to 23° C. After 1 h, the mixture was poured into saturated aqueous NaHCO3 and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic portions were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by FCC (silica gel, 100% hexane followed by 2:1 hexane/CH2Cl2) to afford the above named aldehyde 5.

Provenance & Evidence