Réaction #554634

ord-08e7bcdbab2549c384510081d8f10672

Équation de réaction

[Na+].[OH-]
NaOH
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxy-5α-androstan-17-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
product 7
Rendement 95.1%
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
5α-androstan-3,17-dione
Rendement 95.1%

Réactifs

[Na+].[OH-]
NaOH
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6
C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxy-5α-androstan-17-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent

Réactifs

Aucun

Solvants

CC(C)=O
acetone

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added by drops
  2. 2
    Autreliquid phase was separated
  3. 3
    workup.ADDITION90 ml water was added
  4. 4
    FiltrationThe resulting precipitate was filtered off

Mode opératoire

To the mixture of 6 (5 g, 17.2 mmol) and 75 ml acetone at room temperature 1.5 ml of Jones reagent (CrO3, H2SO4, H2O) was added by drops. After the reaction was completed, NaOH was added, liquid phase was separated and then 90 ml water was added. The resulting precipitate was filtered off to afford product 7 (4.72 g, 94%). M.p. 134-137° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08623849B2uspto-grants-2014_01