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HRID1903002

反应详情

EQUATION

反应方程式

HRID 1903002 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 1340 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 precipitated solid product is removed by filtration. After dissolving in methylene chloride and drying with sodium sulfate, the product is concentrated under vacuum. By trituration of the resultant solid compound with ethyl acetate, 99.8 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is obtained, mp 196.5°-198° C.

WORKUP

后处理

  1. customthe precipitated solid product is removed by filtration
  2. dissolutionAfter dissolving in methylene chloride
  3. dry with materialdrying with sodium sulfate
  4. concentrationthe product is concentrated under vacuum