Dimethyl Sulfoxide → HCID 11078038, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 43.9 g of oxalyl chloride in 0.52 l of dichloromethane, pre-cooled to -70° C., was added over 35 min a solution of 62.9 g of dimethylsulfoxide in 0.10 l of dichloromethane. The solution was stirred for 10 min at -70° C. Then, a solution of 76.5 g of 4-trityloxy-1-butanol in 0.3 l of dichloromethane was added over 35 min, the temperature being maintained at -65° to -70° C. Stirring was continued for another 20 min, and then, 92.9 g of triethylamine were added over 10 min at -60° to -70° C. The mixture was stirred for 20 min at -70° C., and then allowed to warm to 20° C. over 45 min. After the addition of 0.5 l of water, stirring was continued for 15 min. The layers were separated and the aqueous phase was extracted with 0.6 l of dichloromethane. The organic phase was washed with 0.6 l of water and dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was crystallized from hexane to yield 60.7 g of 4-trityloxy-butanal as white crystals of m.p. 62°-65° C.

Provenance & Evidence