Trityl chloride → HCID 131734283, compound

Participants

Reaction Steps

17 grams of 1-(2-octyl)dodecyl-glycerol (dried by azeotropic distillation with benzene) was dissolved in a mixture of dry THF (400 ml) and dry acetonitrile (160 ml). Triphenylchloromethane (15.8 grams) and dry triethylamine (14 ml) were added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was cooled to room temperature, poured on ice (1 kilogram), transferred to a separatory funnel and extracted with diethyl ether (3×200 ml). The combined organic phase was washed consecutively with water (200 ml), dilute (1.5%) sulfuric acid (2×100 ml), water (200 ml), concentrated aqueous sodium bicarbonate (200 ml) and again with water (200 ml). The organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the obtained crude product was purified by chromatography on a silica gel (350 grams) column. 26 grams of pure (S)-1-(2-octyl)dodecyl-3-trityl-glycerol was eluted by hexane followed by a mixtures of hexane and chloroform (50-100%) as a yellow oil. The yield was 92.7%.

Provenance & Evidence