Реакция #93693

ord-7ff38eea68f44483bc43bbb2373e964e

Уравнение реакции

CC(C)(C)[Si](C)(C)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
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid
→
CC(C)OC(C)C
diisopropyl ether
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
7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one

Реактанты

CC(C)(C)[Si](C)(C)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
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid

Реагенты

Нет

Растворители

CCOCC
ether
C1CCOC1
tetrahydrofuran

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Промывкаwashed with saturated sodium bicarbonate solution and water
  2. 2
    Сушкаdried over sodium sulfate
  3. 3
    Концентрированиеconcentrated under vacuum

Методика

142 g of 3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 400 ml of tetrahydrofuran and 400 ml of methanol and stirred with 1,000 ml of 8% strength sulfuric acid for 1.5 hours at room temperature. The mixture is then diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the resultant solid with diisopropyl ether, 108 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one is obtained, mp 173° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04614616uspto-grants-1986_09