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

HRID 2397986Notes

Reaction equation

HRID 2397986 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.C[O-].[Na+].CO>[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

6

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 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

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

Workup

  1. additionis poured onto ice-water
  2. stirringstirred about 30 minutes at room temperature
  3. customThe methanol is removed
  4. customthe residue triturated with water
  5. customThe filtered solid is crystallized from acetone

Sources & evidence

ORD record
ord-74dd7bf986f44a099be36723a76d43c5
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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