Acetonitrile → (2R)-1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Beteiligte Stoffe

Reaktionsschritte

39 grams (113 mmol) of (S)-1-octadecyl-glycerol and 40 grams (137 mmol) of triphenylchloromethane were added to a mixture of 500 ml of dry THF and 130 ml of dry acetonitrile. 32 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), transferred to a separatory funnel and extracted twice with 200 ml diethyl ether. The organic phase was washed consecutively with 200 ml water, twice with 100 ml dilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate, and again with 200 ml water. The solution was then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue, a brown oil, was dissolved in 250 ml ethyl acetate and cooled to −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at a temperature of −10° C. (3500 RPM), and the mother liquid was then poured off. The remaining solid was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 50 grams of pure (R)-1-octadecyl-3-trityl-glycerol.

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