反応 #93694

ord-4f6f033bf183440a905cf0a17ebf7a0c

反応方程式

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
収率 94.4%

反応物

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

試薬

[Zn]
zinc

溶媒

CC(=O)O
acetic acid

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    ろ過The zinc is then filtered off
  2. 2
    workup.ADDITIONthe filtrate is diluted with methylene chloride
  3. 3
    洗浄washed with sodium bicarbonate solution and water
  4. 4
    乾燥After drying over sodium sulfate
  5. 5
    濃縮the product is concentrated under vacuum

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04614616uspto-grants-1986_09