Dimethyl Sulfoxide → HCID 131722601, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (2M; 0.45 ml) and DMSO(0.13 ml) were added to dichloromethane (5 ml) which was previously cooled to −70° C. and the mixture was agitated for 15 minutes. The solution of isopropyl (Z)-9-[(1R,2R,3R,5S)-2-(3,3-ethylene dioxydecyl)-5-hydroxy-3-(tetrahydropyranyloxy)cyclopentyl]-7-nonenoate (3-a)(0.350 g) in dichloromethane (7 ml) was dropped into the mixture. The resultant mixture was warmed to −55° C. and agitated for 15 minutes, and then triethylamine (0.25 ml) was added to the mixture. The resultant mixture was warmed to 10° C. over 6 hours. The crude product obtained by the conventional treatment of the reaction mixture was purified on silica gel column to give the titled compound (5-a)[yield:0.311 g(89%)].

Provenance & Evidence