تفاعل #93694

ord-4f6f033bf183440a905cf0a17ebf7a0c

معادلة التفاعل

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
المردود 94.4%

المتفاعلات

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

الكواشف

[Zn]
zinc

المذيبات

CC(=O)O
acetic acid

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe zinc is then filtered off
  2. 2
    workup.ADDITIONthe filtrate is diluted with methylene chloride
  3. 3
    غسيلwashed with sodium bicarbonate solution and water
  4. 4
    تجفيفAfter drying over sodium sulfate
  5. 5
    تركيزthe product is concentrated under vacuum

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04614616uspto-grants-1986_09