Acetonitrile → HCID 15867795, compound

Participants

Reaction Steps

To a solution of ice-cooled acetonitrile (2 ml) and pyridine (0.2 mL) was added hydrogen fluoride-pyridine (0.2 mL). To this solution was added a mixture (174 mg) containing methyl (11R,12R,13E,15S,17R)-9-methyl-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethylprosta-8,13-dienoate in pyridine (0.2 mL). The ice bath was removed and the solution was agitated for 15 hours while returning it to room temperature. The reaction solution was poured into a mixture of ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The desired product was extracted from this mixed solution with ethyl acetate. The extract was washed with brine, then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, then was purified by silica gel column chromotography (30 to 50% ethyl acetate/hexane) and subjected to thin layer chromotography for separation (ethyl acetate:hexane=4:1) to obtain methyl (11R,12R,13E,15S,17R)-9-methyl-11,15-dihydroxy-17,20-dimethylprosta-8,13-dienoate (21 mg, 2 step 10%) and as a byproduct, methyl (11R,12R,13E,15S,17R)-9-trifluoromethanesulfonyloxy-11,15-dihydroxy-17,20-dimethylprosta-8,13-dienoate (48 mg, 2 step, 18%).

Provenance & Evidence