17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one → 1alpha-Methyl-4-androstene-3,17,19-trione

HRID 1834911Notes

Reaction equation

HRID 1834911 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:22][C@@H:15]1[C@@:16]2([CH:17]=[O:18])[C:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C:2]2=[O:1])=[CH:12][C:13](=[O:23])[CH2:14]1

Participants

4

Reactant 2

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-oneHCID 131709961Jones' reagent

Product 1

HCID 543865421alpha-Methyl-4-androstene-3,17,19-trione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one in acetone at 20° C. is added 2 equivalents of Jones Reagent with stirring. After 15 minutes the upper acetone layer is decanted and poured onto ice water and stirred for an additional 30 minutes. The precipitate which forms is filtered, washed with water and dissolved in ether. The ether solution is dried over magnesium sulfate and concentrated under reduced pressure. The residue is crystallized from acetone-hexane to yield 1α-methyl-4-androstene-3,17,19-trione.

Workup

  1. customAfter 15 minutes the upper acetone layer is decanted
  2. additionpoured onto ice water
  3. stirringstirred for an additional 30 minutes
  4. filtrationThe precipitate which forms is filtered
  5. washwashed with water
  6. dissolutiondissolved in ether
  7. dry with materialThe ether solution is dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is crystallized from acetone-hexane

Sources & evidence

ORD record
ord-769ba33e210c4f7a96e29ab184bee3b5
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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