Pyridine → HCID 67859862, compound

Participants

Reaction Steps

A solution of 1.0 g of (13E)-(8R,9S,11R,12R,15S)-9-hydroxy-19-methyl-11,15-bis(tetrahydropyran-2-yloxy)-13,18-prostadienoic acid methyl ester in 14 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile was stirred together with 730 mg of triphenylphosphine for 70 hours at room temperature under argon. Thereafter the mixture was diluted with 16 ml of ether and 32 ml of hexane, further agitated for 10 minutes, filtered, and concentrated by means of a forced circulation evaporator. The evaporation residue was extracted with a mixture of 5 ml of ether and 95 ml of hexane, filtered, and concentrated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/20% ethyl acetate as the eluent, thus obtaining 720 mg of the title compound.

Provenance & Evidence