Methyl Ethyl Ketone → Androst-4,7-diene-3,17-dione

HRID 1708902Notes

Reaction equation

HRID 1708902 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].CC(=O)CC.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(C)C=CC=CC=1>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 11143Aluminum isopropoxideHCID 9817420Androsta-5,7-diene-3b,17b-diol

Product 1

HCID 14369573Androst-4,7-diene-3,17-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of androst-5,7-diene-3β,17β-diol (2.9 g, 10 mmol) in 150 ml toluene is azeotropically dried for one hour. Butanone (15 ml) is added followed by aluminum isopropoxide (1.7 g, 8 mmol) and the mixture is heated at reflux for 2.5 hours. The solution is then concentrated to a volume of 25 ml, diluted with trichloromethane, and washed with 5% hydrochloric acid, aqueous sodium bicarbonate, and brine. Concentration and chromatography affords androst-4,7-diene-3,17-dione.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe solution is then concentrated to a volume of 25 ml
  4. additiondiluted with trichloromethane
  5. washwashed with 5% hydrochloric acid, aqueous sodium bicarbonate, and brine
  6. concentrationConcentration and chromatography

Sources & evidence

ORD record
ord-ef84fe8dd89b4af1910948ea4a4e09c9
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Reaction notes

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