17beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-one → 1alpha,7alpha-Dimethyl-4-androstene-3,17,19-trione

HRID 2398001Notes

Reaction equation

HRID 2398001 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][C@H:9]3[CH3:24].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][C@@H:9]([CH3:24])[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 7058545317beta,19-Dihydroxy-1alpha,7alpha-dimethyl-4-androsten-3-oneHCID 131709961Jones' reagent

Product 1

HCID 538793401alpha,7alpha-Dimethyl-4-androstene-3,17,19-trione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 17β, 19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one in acetone at 20° C. is added two equivalents of Jones Reagent and the mixture stirred for 30 minutes. The acetone layer is poured onto water with vigorous stirring. The crystals are removed by suction filtration and air dried. Crystallization from an acetone-hexane solution yields 1α,7α-dimethyl-4-androstene-3,17,19-trione.

Workup

  1. customThe crystals are removed by suction filtration and air
  2. customdried
  3. customCrystallization from an acetone-hexane solution

Sources & evidence

ORD record
ord-f6058e870a3946d49f9a09ea884149c3
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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