Реакция #93696

ord-f765bf6307e449e099e316345420dbcd

Уравнение реакции

C[C@]12CC[C@H]3[C@@H]([C@@H](O)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one
ClCCl
methylene chloride
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
→
C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one

Реактанты

C[C@]12CC[C@H]3[C@@H]([C@@H](O)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one
ClCCl
methylene chloride
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine

Реагенты

Нет

Растворители

ClC(Cl)(Cl)Cl
carbon tetrachloride
c1ccncc1
pyridine

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ПромывкаThe mixture is then washed with water
  2. 2
    Сушкаdried over sodium sulfate
  3. 3
    Концентрированиеconcentrated under vacuum

Методика

24 g of 3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one is dissolved in a mixture of 250 ml of methylene chloride, 250 ml of carbon tetrachloride, and 125 ml of pyridine and stirred with 24 g of triphenylphosphine for 3 hours. The mixture is then washed with water, dried over sodium sulfate, and concentrated under vacuum. After chromatography on silica gel with hexane-acetone, 19.8 g of 3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is obtained.

Источник

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