Sodium Carbonate → 17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

HRID 2397965Notes

Reaction equation

HRID 2397965 reaction equation
C(O)(=O)CC.C(O)(=O)CC.[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:33])[CH2:24][C@@H:25]1[CH3:32])[CH2:20][CH2:19]3

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 8673472917beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one dipropionate

Product 1

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one dipropionate in methanol is refluxed for about two hours with aqueous sodium carbonate. The solvent is removed and the residue dissolved in chloroform. The chloroform extract is washed well with water, dried over magnesium sulfate and evaporated under vacuum. The residue which remains is crystallized from acetonitrile to yield 17β,19-dihydroxy-1α-methyl-4-androsten-3-one.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in chloroform
  3. extractionThe chloroform extract
  4. washis washed well with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue which remains is crystallized from acetonitrile

Sources & evidence

ORD record
ord-dd3b3b4b66ec48418fe4d71651ba688a
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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