反应详情

温度

0 °C

To a solution of 35.5 g (181 mmol) of (-)-1-benzoyl glycerol (G) in 250 ml of dry pyridine at 0° C. is added 83 g (433 mmol) of p-toluenesulfonyl chloride. The mixture is stirred at 0° C. for 15 minutes and then stored in a refrigerator for 144 hours. After cooling the reaction mixture to 0° C., 10 ml of water are added, the mixture is stirred for 10 minutes, and then poured into excess water. The aqueous solution is separated from the gummy product, and extracted with chloroform. The gummy residue is dissolved in chloroform and the combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water. The chloroform solution is dried over Na2SO4 and concentrated under reduced pressure to obtain a solid which, upon recrystallization from absolute ethanol, gives 65.5 g (130 mmol, 72%) of (-)-1-benzoyl-2,3-di-p-toluenesulfonyl glycerol (see Formula (H) in Scheme 2), m.p. 105°-106° C. [α]D2° -22.7 (c, 5.92, CHCl3). 1H NMR (CDCl3) δ8-7 (m, 13H); 4.9 (m, 1H); 4.45 (d, 2H, J=6 Hz); 4.35 (d, 2H, J=5 Hz); 2.42 (s, 3H); 2.38 (s, 3H). 13C NMR (CDCl3) 165.162, 145.136, 133.108, 132.466, 131.649, 129.430, 128.671, 128.087, 127.678, 75.306, 66.899, 61.994, 21.591 ppm.

1. waitstored in a refrigerator for 144 hours
2. temperatureAfter cooling the reaction mixture to 0° C.
3. stirringthe mixture is stirred for 10 minutes
4. customThe aqueous solution is separated from the gummy product
5. extractionextracted with chloroform
6. dissolutionThe gummy residue is dissolved in chloroform
7. washthe combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water
8. dry with materialThe chloroform solution is dried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customto obtain a solid which
11. customupon recrystallization from absolute ethanol