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

HRID 1834975Notes

Reaction equation

HRID 1834975 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

1β,2β-Methylene-5-androstene-3β,17β-diol is dissolved in acetone and Jones reagent is added until a persistent yellow orange color appears. After stirring at room temperature for 10 minutes the mixture is poured onto icewater. The precipitate is collected by filtration and dissolved in a solution of sodium methoxide in methanol. Stirring is continued for about 30 minutes at room temperature, the methanol is removed and the residue triturated with water. The solid is filtered and crystallized from acetone to yield 1β,2β-methylene-4-androstene-3,17-dione.

Workup

  1. additionis poured onto icewater
  2. filtrationThe precipitate is collected by filtration
  3. dissolutiondissolved in a solution of sodium methoxide in methanol
  4. stirringStirring
  5. waitis continued for about 30 minutes at room temperature
  6. customthe methanol is removed
  7. customthe residue triturated with water
  8. filtrationThe solid is filtered
  9. customcrystallized from acetone

Sources & evidence

ORD record
ord-e7226072ddf64fc5ab43f0b5f1b6ccac
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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