(Diethylamino)trimethylsilane → Prostaglandin E2

Participants

Reaction Steps

A solution of 1.07 g of PGF2=, 1,15-lactone in 45 ml of anhydrous acetone was cooled under nitrogen to between -45° and -40° and treated with 4.5 ml of trimethylsilyldiethylamine. After the addition was complete (2-3 min.), the mixture was stirred at -42° ± 2° C. for 2 hours, by which time TLC (25% ethyl acetate/hexane) showd only a trace of starting material. The reaction mixture was then cooled to -78° , diluted with 150 ml of precooled ether (-78° ) and poured into ice/brine. After extraction with hexane, the combined organic layers were washed with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the mono-trimethylsily derivative of PGE2α, 1,15-lactone.

Provenance & Evidence