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

Participants

Reaction Steps

19.83 grams of (S)-1-dodecyl-glycerol and 21.0 grams of triphenylchloromethane were added to a mixture of 250 ml dry tetrahydrofuran (THF) and 60 ml dry acetonitrile. 22 ml of dry triethylamine was added and the reaction mixture was refluxed for 17 hours under nitrogen. The reaction mixture was then cooled to room temperature, and 5 ml triethylamine and 10 grams of ice were added. The mixture was transferred to a separatory funnel and extracted with 100 ml MTBE. The organic phase was washed consecutively with 150 ml water, 150 ml of dilute (1.5%) H2SO4, 150 ml water, 150 ml of concentrated aqueous sodium bicarbonate, and again with 150 ml water. The solution was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The residue, 40.63 grams of a brown oil, was dissolved in 200 ml ethyl acetate and cooled to −20° C. for a couple of days. The mixture was centrifuged at a temperature of −10° C. and the mother liquid was poured off. The solid melted at room temperature and was purified by chromatography on a silica gel column (195 grams). 18.57 grams of pure (R)-1-dodecyl-3-trityl-glycerol was eluted by mixtures of chloroform and hexane followed by a mixture of 9:1 (v/v) chloroform:ethyl acetate. The yield was 48.5%.

Provenance & Evidence