7-Thia-13-prostynoic acid → 7-Thiaprostanoic Acid

Participants

Reaction Steps

To a suspension of 50 mg of 10% palladium on charcoal in 1 ml of ethyl acetate, which had been pre-reduced with hydrogen gas was added 7-thia-13-prostynoic acid (15 mg) in 1.5 ml of ethyl acetate. After 5 hrs the catalyst was removed by filtration washed with ethyl acetate and the combined filtrates evaporated to yield 13 mg of a semisolid. Analysis by nmr indicated that there still remained starting material plus some 7-thia-13-cis-prostenoic acid. The material was therefore reduced again with 50 mg of fresh palladium catalyst for 1/2 hour and the reduced material isolated by filtration and removal of the solvent. 8 Milligrams of the saturated acid was obtained, which after recrystallization from hexane melted at 40°-41°.

Provenance & Evidence