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

Participants

Reaction Steps

A solution of 35.3 grams of 1-hexadecyl-sn-glycerol, 37.3 grams of triphenylchloromethane and 22.44 grams of dry triethylamine in a mixture of 470 ml dry tetrahydrofuran and 120 ml dry acetonitrile was refluxed for 15 hours under a nitrogen atmosphere. After cooling to room temperature the reaction mixture was filtered. The filtrate poured on ice (500 grams) and then extracted thrice with 200 ml chloroform. The organic phase was washed successively with 500 ml water, 500 ml of 0.15 N HCl, 500 ml saturated aqueous NaHCO3, and again with water. The extract was dried over Na2SO4 and the solvent was removed under reduced pressure. The obtained yellow residue was dissolved in 500 ml warm hexane and the obtained clear solution was refrigerated (5±3° C.) overnight. During this time, precipitation occurred. After filtration of the precipitate, the solvent from the filtrate was removed under reduced pressure, yielding 58.3 grams of 1-hexadecyl-3-trityl-sn-glycerol. The yield was 95%.

Provenance & Evidence