Triethylamine → 2-(Benzoyloxy)-3-(octadecyloxy)propyl 10-trimethylammoniodecyl phosphate

Participants

Reaction Steps

2.24 g (5.0 mmole) of 2-benzoyloxy-3-octadecyloxypropanol was dissolved in 20 ml of ethanol-free chloroform and 2.63 g (26.0 mmole) of dry triethylamine was added thereto under ice-cooling. Then, 0.81 g (5.3 mmole) of phosphorus oxychloride in 40 ml of ethanol-free chloroform was further added, and the resulting mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1 hour. This reaction mixture was again cooled on ice, and 2.80 g (7.5 mmole) of 10-trimethylammoniodecylalcohol monotosylate in 80 ml of dry pyridine was added thereto. The reaction mixture was stirred under ice-cooling for 30 minutes and at room temperature for 18 hours. To the reaction mixture was added an aqueous solution containing 3.5 g sodium hydrogencarbonate and the resulting mixture was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on Amberlite resin (IR-120: IRA-410=1:2; eluent: 95% THF) and then further by column chromatography on silica gel (Merck, Art 7734; eluent: chloroform-methanol-water=65:25:4) to give 1.57 g (yield: 43.4%) of the desired product.

Provenance & Evidence