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HRID65416

反应详情

EQUATION

反应方程式

HRID 65416 的结构方程式

REACTANTS

反应物

2
结构：C1CCOC1
HCID8028

Tetrahydrofuran

C4H8O

结构：C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
HCID13075966

未命名化合物

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 94.4%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：[Zn]
催化剂HCID23994

Zinc

Zn

结构：CC(=O)O
溶剂HCID176

Acetic Acid

C2H4O2

PROCEDURE

实验过程

107.5 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 500 ml of acetic acid and 500 ml of tetrahydrofuran and, after the addition of 324 g of zinc dust in three portions, stirred at room temperature for 16 hours. The zinc is then filtered off, the filtrate is diluted with methylene chloride, and washed with sodium bicarbonate solution and water. After drying over sodium sulfate, the product is concentrated under vacuum. By trituration of the thus-obtained solid with ethyl acetate, 91.5 g of 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one is produced, mp 196° C.

WORKUP

后处理

  1. filtrationThe zinc is then filtered off
  2. additionthe filtrate is diluted with methylene chloride
  3. washwashed with sodium bicarbonate solution and water
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe product is concentrated under vacuum