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HRID65413

反应详情

EQUATION

反应方程式

HRID 65413 的结构方程式

REACTANTS

反应物

4
结构：O=S(=O)(O)O
HCID1118

Sulfuric acid

H2O4S

结构：[K+].[OH-]
HCID14797

Potassium hydroxide

HKO

结构：[Na+].[O-][Cl+3]([O-])([O-])[O-]
HCID522606

Sodium perchlorate

ClNaO4

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]3C=C[C@]2(O)C1
HCID13075972

5-Hydroxy-15 beta,16 beta-methylene-3 beta-pivaloyloxy-5 beta-androst-6-en-17-one

C25H36O4

PRODUCTS

生成物

1
结构：C[C@]12CC[C@H]3[C@@H](C=C[C@]4(O)C[C@@H](O)CC[C@]34C)[C@@H]1[C@@H]1C[C@@H]1C2=O
HCID13075974

(2S,4aR,4bS,6aS,7aS,8aS,8bS,10aR)-2,10a-Dihydroxy-4a,6a-dimethyl-2,3,4,4a,4b,5,6,6a,7a,8,8a,8b,8c,10a-tetradecahydrocyclopropa[4,5]cyclopenta[1,2-a]phenanthren-7(1H)-one

C20H28O3

收率 94.3%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CO
溶剂HCID887

Methanol

CH4O

结构：O
溶剂HCID962

Water

H2O

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

134 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is dissolved in 1,340 ml of tetrahydrofuran and 670 ml of methanol and combined in succession with 40 g of pulverized potassium hydroxide and 13 g of sodium perchlorate. After 2.5 hours, the mixture is stirred into 8 l of water, neutralized with 20% sulfuric acid, and the thus-precipitated solid is filtered off. After dissolving the solid in methylene chloride and drying same with sodium sulfate, it is concentrated under vacuum. By trituration of the resultant solid with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 198° C.

WORKUP

后处理

  1. filtrationthe thus-precipitated solid is filtered off
  2. dissolutionAfter dissolving the solid in methylene chloride
  3. dry with materialdrying same with sodium sulfate, it
  4. concentrationis concentrated under vacuum