Реакция #93694

ord-4f6f033bf183440a905cf0a17ebf7a0c

Уравнение реакции

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
C1CCOC1
tetrahydrofuran
→
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
3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one
Выход 94.4%

Реактанты

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
C1CCOC1
tetrahydrofuran

Реагенты

[Zn]
zinc

Растворители

CC(=O)O
acetic acid

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ФильтрацияThe zinc is then filtered off
  2. 2
    workup.ADDITIONthe filtrate is diluted with methylene chloride
  3. 3
    Промывкаwashed with sodium bicarbonate solution and water
  4. 4
    СушкаAfter drying over sodium sulfate
  5. 5
    Концентрированиеthe product is concentrated under vacuum

Методика

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.

Источник

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