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HRID1649463

反应详情

EQUATION

反应方程式

HRID 1649463 的结构方程式

REACTANTS

反应物

3
结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：Cl[Si](Cc1ccccc1)(Cc1ccccc1)Cc1ccccc1
HCID87774

Silane, chlorotris(phenylmethyl)-

C21H21ClSi

结构：C[C@]12CC[C@H](O)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
HCID44520204

未命名化合物

PRODUCTS

生成物

1
结构：C[C@]12CC[C@H](O[Si](Cc3ccccc3)(Cc3ccccc3)Cc3ccccc3)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
HCID70466968

未命名化合物

收率 89.8%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccccn1
催化剂HCID21885

2-Dimethylaminopyridine

C7H10N2

结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

3 次

CONDITIONS

反应条件

温度
-20 °C

PROCEDURE

实验过程

A solution of 15.7 g of 3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one in 750 ml of methylene chloride is combined with 9 ml of triethylamine and 200 mg of dimethylaminopyridine and cooled to -20° C. Within 30 minutes, 19.4 g of tribenzylsilyl chloride in 10 ml of methylene chloride is added dropwise thereto. The reaction mixture is stirred for one hour at -20° C. and one hour at 0° C., diluted with methylene chloride, and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution, and water. After drying over sodium sulfate, the mixture is concentrated under vacuum. Chromatography on silica gel with hexane-acetone yields 27.5 g of 3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one.

WORKUP

后处理

  1. washwashed with 1 N hydrochloric acid, saturated sodium bicarbonate solution, and water
  2. dry with materialAfter drying over sodium sulfate
  3. concentrationthe mixture is concentrated under vacuum