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HRID652271

反应详情

EQUATION

反应方程式

HRID 652271 的结构方程式

REACTANTS

反应物

1
结构：CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=CC4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
HCID13519086

(1β,2β)-17-(Acetyloxy)-1,2-dihydro-3′H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione

C24H30O4

PRODUCTS

生成物

1
结构：CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
HCID13519088

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：O=C([O-])[O-].[Ca+2].[Pd]
催化剂HCID12000666

未命名化合物

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of 60.0 g of 17α-acetoxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione [R. Wiechert et al., Chem. Ber. 93: 1710 (1960)] in 1.25 1 of dimethylformamide is combined with 6.3 g of 10% Pd/CaCO3 and then hydrogenated. After a hydrogen absorption of 5.1 1, the catalyst is filtered off and the reaction solution stirred into ice water. The precipitate is suctioned off, worked up as usual, and the crude product is purified on 1.5 kg of silica gel with a pentane-acetone gradient (0-30% acetone). Yield: 34.3 g of 17α-acetoxy-1α,2α-methylene-4-pregnene-3,20-dione, mp 268°-270° C. [α]D =+215°.

WORKUP

后处理

  1. customAfter a hydrogen absorption of 5.1 1
  2. filtrationthe catalyst is filtered off
  3. customis purified on 1.5 kg of silica gel with a pentane-acetone gradient (0-30% acetone)
  4. customYield: 34.3 g of 17α-acetoxy-1α,2α-methylene-4-pregnene-3,20-dione, mp 268°-270° C. [α]D =+215°