Isopropanol → HCID 86744831, compound

Participants

Reaction Steps

The solution of 396 mg of (13E)-(9S,11R,15S,16RS)-6-oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)-16-methyl-18,18,19,19-tetradehydro-13-prostenoic acid in 8 ml of absolute dimethylketone was cooled, with exclusion of moisture, to -30° C., was mixed with 270 microliters of Jones solution and stirred for 1.5 h at -30° C. to -20° C. After addition of 2 ml of isopropanol, it was poured onto 50 ml of ice water, extracted several times with a total of 100 ml of diethyl ether, washed neutral with saturated sodium chloride solution, dried on magnesium sulfate, filtered and concentrated by evaporation in a vacuum. The colorless raw oil was chromatographed on plates coated with silica gel with hexane-ethyl acetate. Besides the initial material, 160 mg (41%) of the title compound was isolated as colorless oil.

Provenance & Evidence