HRID1903001

反应详情

EQUATION

反应方程式

REACTANTS

反应物

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

PRODUCTS

生成物

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

收率 74.6%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23994

Zinc

溶剂HCID176

Acetic Acid

C2H4O2

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of 196 g of 7α-chloro-5,6β-epoxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one in 500 ml of acetic acid and 800 ml of tetrahydrofuran is combined at 70° C. with 392 g of zinc dust in two portions at an interval of 30 minutes and stirred for one hour at this temperature. After cooling, the zinc is filtered off over "Celite" and washed with 5 l of methylene chloride. The combined filtrates are combined with 1.5 l of water and neutralized under agitation by adding solid sodium bicarbonate. The organic phase is then washed with water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the resultant solid product with ethyl acetate, 134.7 g of 5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one is obtained, mp 242°≥243° C.

WORKUP

后处理

temperatureAfter cooling
filtrationthe zinc is filtered off over "Celite"
washwashed with 5 l of methylene chloride
additionby adding solid sodium bicarbonate
washThe organic phase is then washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum