1beta,2beta-Methylene-5-androstene-3beta,17beta-diol → 1beta,2beta-Methylene-4-androstene-3,17-dione

HRID 371846Notes

Reaction equation

HRID 371846 reaction equation
[CH2:1]1[C@@H:3]2[C@H:4]([OH:22])[CH2:5][C:6]3[C@:19]([CH3:20])([C@H:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C@@H:13]([OH:21])[CH2:12][CH2:11]2)[CH2:8][CH:7]=3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([C@H:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3

Participants

4

Reactant 2

HCID 566286851beta,2beta-Methylene-5-androstene-3beta,17beta-diolHCID 131709961Jones' reagent

Product 1

HCID 542623781beta,2beta-Methylene-4-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The 1β,2β-methylene-5-androstene-3β,17β-diol is dissolved in acetone and Jones reagent added until a persistent yellow-orange color appears. After stirring at room temperature for ten minutes the mixture is poured onto ice-water and the precipitate is collected by filtration. The precipitate is dissolved in a solution of sodium methoxide in methanol and stirred for a period of 30 minutes at room temperature. The methanol is removed and the residue triturated with water. The solid which results is filtered and crystallized from acetone to yield 1β,2β-methylene-4-androstene-3,17-dione.

Workup

  1. additionis poured onto ice-water
  2. filtrationthe precipitate is collected by filtration
  3. dissolutionThe precipitate is dissolved in a solution of sodium methoxide in methanol
  4. stirringstirred for a period of 30 minutes at room temperature
  5. customThe methanol is removed
  6. customthe residue triturated with water
  7. customThe solid which results
  8. filtrationis filtered
  9. customcrystallized from acetone

Sources & evidence

ORD record
ord-418bc839e03d4f55af1df74410c7c3b8
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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