HRID1650361

反应详情

EQUATION

反应方程式

HRID 1650361 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

544 mg (1 mmol) of 10-deacetylbaccatine III, dissolved in 50 cm3 of anhydrous pyridine, are introduced under an argon atmosphere into a 100-cm3 round-bottomed flask equipped with a magnetic stirrer. 3.36 cm3 (3.014 g; 20 mmol) of triethylsilyl chloride are then added. The homogeneous, yellow reaction mixture is then stirred for 24 hours at 0° C. Ethyl acetate and water are then added. After settling has taken place, the separated aqueous phase is extracted with ethyl acetate. The combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine has been completely removed. The organic phases are washed with water and then with saturated sodium chloride solution, and then dried over anhydrous sodium sulphate. After filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product are obtained, and this is purified on a silica column, eluting with a dichloromethane/methanol (99:1 by volume) mixture. 512 mg (0.778 mmol) of 10-deacetyl-7-triethylsilylbaccatine III are thereby obtained, in a 78% yield, in the form of a white solid, the characteristics of which are as follows:

WORKUP

后处理

  1. additionare introduced under an argon atmosphere into a 100-cm3 round-bottomed flask
  2. customequipped with a magnetic stirrer
  3. extractionthe separated aqueous phase is extracted with ethyl acetate
  4. additionThe combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine
  5. customhas been completely removed
  6. washThe organic phases are washed with water
  7. dry with materialwith saturated sodium chloride solution, and then dried over anhydrous sodium sulphate
  8. filtrationAfter filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product
  9. customare obtained
  10. customthis is purified on a silica column
  11. washeluting with a dichloromethane/methanol (99:1 by volume) mixture