Acetonitrile → (R)-1-hexadecyl-3-trityl-glycerol

Participants

Reaction Steps

40 grams of 1-hexadecyl-glycerol and 43 grams triphenylchloromethane were added to a mixture of 500 ml dry tetrahydrofuran and 130 ml dry acetonitrile. 35 ml of dry triethylamine was added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature, poured on ice (1 kilogram) and extracted thrice with 250 ml diethyl ether. The organic phase was washed consecutively with 100 ml water, 100 ml dilute (1.5%) sulfuric acid, 100 ml water, 100 ml concentrated aqueous sodium bicarbonate and again with 100 ml water. The obtained organic phase was dried over anhydrous sodium sulfate and the solvent was thereafter removed under reduced pressure. The residue was dissolved in 200 ml ethyl acetate and the resulting solution was cooled at −20° C. overnight. The mixture was then centrifuged at −5° C. and the mother liquid solution was poured off. The solid was dissolved in hexane and refrigerated overnight at 5° C. Filtration of the precipitate yielded pure 1-hexadecyl-3-trityl-sn-glycerol.

Provenance & Evidence