Pyridine → HCID 67859585, compound

Participants

Reaction Steps

A solution of 1.09 g of (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid methyl ester, 760 mg of triphenylphosphine, and 14.5 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile were agitated under argon at room temperature for 69 hours. The mixture was then diluted with 15 ml of ether and 30 ml of hexane, further stirred for 10 minutes, and filtered. The residue from the evaporation was extracted with a mixture of 5 ml of ether and 95 ml of hexane, filtered, and evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/20-33% ethyl acetate as the eluent, thus isolating 1.04 g of the desired compound.

Provenance & Evidence