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

Participants

Reaction Steps

20 grams of (S)-1-hexadecyl-glycerol and 21.29 grams of triphenylchloromethane were dissolved in 369 ml dry tetrahydrofuran (THF) and 93 ml dry acetonitrile. 17.75 ml triethylamine was added and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (100 grams), transferred to a separatory funnel and extracted with methyl tert-butyl 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 give 36.86 grams of crude product as a residue. This residue was dissolved in hot hexane (200 ml) and the resulting solution was cooled at 4° C. overnight. The precipitated product was filtered, yielding 30.71 grams of (R)-1-hexadecyl-3-trityl-glycerol.

Provenance & Evidence