Reaction #554634

ord-08e7bcdbab2549c384510081d8f10672

Reaction equation

[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
Yield 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
Yield 95.1%

Reactants

[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

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US08623849B2uspto-grants-2014_01