Acetonitrile → HCID 67230477, compound

Participants

Reaction Steps

34 grams of (S)-1-octyl-glycerol and 61 grams of triphenylchloromethane were added to a mixture of 500 ml of dry THF and 130 ml of dry acetonitrile. 46 ml of dry triethylamine was added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature and poured on ice (1 kilogram). The mixture was transferred to a separatory funnel and extracted thrice with 200 ml diethyl ether. The organic phase was washed consecutively with 150 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 Na2SO4 and the solvent was removed under reduced pressure. The obtained residue, 80 grams of a brown oil, was dissolved in 500 ml hot hexane and kept at a temperature of 4° C. overnight. The precipitate was filtered off and the solvent from the filtrate was removed under reduced pressure. The obtained residue was purified by chromatography on silica gel. The resulting pure (R)-1-octyl-3-trityl-glycerol was eluted by mixtures of chloroform with 10% hexane, chloroform with 5% hexane, followed by chloroform with ethyl acetate (5% and 10%). The yield was 73%.

Provenance & Evidence