反应详情

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.

1. temperatureunder ice-cooling
2. temperatureThis reaction mixture was again cooled on an ice bath
3. stirringThe resulting mixture was stirred under ice-
4. temperaturecooling for 30 minutes and at room temperature for 16 hours
5. additionwas added to the reaction mixture
6. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
7. customThe 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)