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

Participants

Reaction Steps

2.34 g (5.4 mmole) of 2-benzyloxy-3-octadecyloxypropanol was dissolved in 20 ml of ethanol-free chloroform and 2.83 g (28.0 mmole) of dry triethylamine was added thereto under ice-cooling. Then, 0.87 g (5.7 mmole) of phosphorus oxychloride in 40 ml of ethanol-free chloroform was further added. The reaction mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1 hour. This reaction mixture was again cooled on an ice bath and 3.00 g (8.07 mmole) of 10-trimethylammoniodecylalcohol monotosylate in 80 ml of dry pyridine was added to the mixture. The resulting mixture was stirred under ice-cooling for 30 minutes and at room temperature for 16 hours. An aqueous solution containing 3.8 g of sodium hydrogencarbonate was added to the reaction mixture and the reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by Amberlite resin column chromatography (IR-120: IRA-410=1:2; eluent: 95% THF) and by silica gel column chromatography (Merck & Co., Art. 7734, eluent: chloroform-methanol:water=65:25:4) to give 1.32 g (yield: 34.3%) of the desired product.

Provenance & Evidence