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HRID65411

反应详情

EQUATION

反应方程式

HRID 65411 的结构方程式

REACTANTS

反应物

4
结构：ClC(Cl)(Cl)Cl
HCID5943

Carbon tetrachloride

CCl4

结构：ClCCl
HCID6344

Dichloromethane

CH2Cl2

结构：c1ccc(P(c2ccccc2)c2ccccc2)cc1
HCID11776

Triphenylphosphine

C18H15P

结构：CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@@H](O)[C@H]3O[C@]32C1
HCID13075958

5beta,6beta-Epoxy-7beta-hydroxy-15beta,16beta-methylene-3beta-pivaloyloxy-5 beta-androstan-17-one

C25H36O5

PRODUCTS

生成物

1
结构：CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
HCID13075960

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

A solution of 169 g of 5,6β-epoxy-7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one in a mixture of respectively 340 ml of dichloromethane, tetrachloromethane, and pyridine is combined with 200 g of triphenylphosphine and stirred for 2 hours at room temperature. The reaction solution is washed with water, dried over sodium sulfate, and evaporated to dryness under vacuum. The residue is stirred up with 310 ml of ethanol and filtered. The filter cake is washed with 175 ml of ethanol and dried under vacuum, thus obtaining 139.2 g of 7α-chloro-5,6β-epoxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one. An analytical sample, recrystallized from acetone-hexane, has a melting point of 228° C. [α]D =-100° (chloroform).

WORKUP

后处理

  1. washThe reaction solution is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness under vacuum
  4. stirringThe residue is stirred up with 310 ml of ethanol
  5. filtrationfiltered
  6. washThe filter cake is washed with 175 ml of ethanol
  7. customdried under vacuum