Sodium Carbonate → 17beta-Hydroxy-1alpha-methyl-4-androsten-19-one

HRID 2397979Notes

Reaction equation

HRID 2397979 reaction equation
C(O)(=O)CC.[OH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:24]([CH2:25][CH2:26][C@:8]12[CH3:9])[C@:21]1([CH:22]=[O:23])[C:16](=[CH:17][CH2:18][CH2:19][C@@H:20]1[CH3:27])[CH2:15][CH2:14]3.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:24]([CH2:25][CH2:26][C@:8]12[CH3:9])[C@:21]1([CH:22]=[O:23])[C:16](=[CH:17][CH2:18][CH2:19][C@@H:20]1[CH3:27])[CH2:15][CH2:14]3

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 8673473517beta-Hydroxy-1alpha-methyl-4-androsten-19-one propionate

Product 1

HCID 8673473617beta-Hydroxy-1alpha-methyl-4-androsten-19-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 17β-hydroxy-1α-methyl-4-androsten-19-one propionate and sodium carbonate in aqueous methanol is refluxed under nitrogen for approximately 2 hours and poured onto water. The oil which forms is extracted with ether. The ether extract is washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue which remains is eluted from silica gel with benzene and crystallized from hexane to yield 17β-hydroxy-1α-methyl-4-androsten-19-one.

Workup

  1. additionpoured onto water
  2. extractionThe oil which forms is extracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue which remains is eluted from silica gel with benzene
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-b1f3193195c2446bae13c3f96ddee847
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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