Реакция #367034

ord-5b2cce0c8dd749659a28ec4a0d0934b9

Уравнение реакции

CCOC(C)=O
ethyl acetate
C[C@H]1CC2(C[C@@H]3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31C)OCCO2
3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol
[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1
pyridinium dichromate
→
C[C@H]1CC2(C[C@@H]3CC[C@@H]4[C@H](CC[C@]5(C)C(=O)CC[C@@H]45)[C@]31C)OCCO2
3,3-ethylenedioxy-1α-methyl-5α-androstan-17-one
Выход 100.6%

Реактанты

CCOC(C)=O
ethyl acetate
C[C@H]1CC2(C[C@@H]3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31C)OCCO2
3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol
[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1
pyridinium dichromate

Реагенты

[Cr]
chromium

Растворители

CN(C)C=O
dimethylformamide

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеby decanting
  2. 2
    Промывкаthe organic phase is washed with water
  3. 3
    ДругоеAfter drying
  4. 4
    Другоеevaporation

Методика

35 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol is stirred in 350 ml of dimethylformamide with 70 g of pyridinium dichromate for 17 hours at room temperature. The reaction solution is stirred into ten times the amount of ethyl acetate, then the thus-separated chromium salts are left behind by decanting, and the organic phase is washed with water. After drying and evaporation, 35 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17-one is produced, mp 154° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04587235uspto-grants-1986_05