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HRID1182879

反应详情

EQUATION

反应方程式

HRID 1182879 的结构方程式

REACTANTS

反应物

3
结构：ClCCl
HCID6344

Dichloromethane

CH2Cl2

结构：O=C(OO)c1cccc(Cl)c1
HCID70297

Benzenecarboperoxoic acid, 3-chloro-

C7H5ClO3

结构：CCC1=C(OC(C)=O)CC[C@@]2(C)C1=CC[C@H]1[C@@H]3CC[C@H](OC(C)=O)[C@@]3(C)CC[C@@H]12
HCID68731244

未命名化合物

PRODUCTS

生成物

2
结构：CCC1=C2[C@H](O)C[C@H]3[C@@H]4CC[C@H](OC(C)=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O
HCID68732269

未命名化合物

收率 105%
结构：CCC1=C2[C@@H](O)C[C@H]3[C@@H]4CC[C@H](OC(C)=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O
HCID68733032

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)OC(C)C.CO
溶剂HCID21882575

未命名化合物

PROCEDURE

实验过程

To a stirred solution of 3,17β-diacetoxy-4-ethylandrosta-3,5-diene (1.08 g) in EtOH/H2O 95/5 (13.7 ml), mCPBA (1.0 g) was added. After 8 h at RT, DCM (150 ml) was added and the mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine. The organic phase was dried over Na2SO4, and evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40) to give a mixture 6α-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one and 6β-hydroxy-17β-acetoxy-4-ethylandrost-4-en-3-one (0.53 g, 52%).

WORKUP

后处理

  1. washthe mixture was washed with 10% Na2SO3 aqueous solution, 5% aqueous NaHCO3 solution, and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)