Trityl chloride → (R)-1-hexadecyl-3-trityl-glycerol

Participants

Reaction Steps

18.47 grams of (S)-1-hexadecyl-sn-glycerol and 19 grams of triphenylchloromethane were dissolved in a mixture of 250 ml dry THF and 58 ml dry acetonitrile. 17 ml of triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (20 grams) and triethylamine (5 ml), transferred to a separatory funnel and extracted with diethyl ether. The organic phase was washed consecutively with 200 ml water, twice with 200 ml dilute (1.5%) sulfuric acid, 200 ml water, 200 ml saturated aqueous sodium bicarbonate, and again with 200 ml water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 41.79 grams of crude product as a residue. This residue was dissolved in 300 ml ethyl acetate and cooled at −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at −10° C., and the mother liquid was poured of. The obtained solid melted and was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 18.97 grams of pure (R)-1-hexadecyl-3-trityl-sn-glycerol as an off-white solid.

Provenance & Evidence