Acetone → HCID 53660110, compound

HRID 440440Notes

Reaction equation

HRID 440440 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C@:15]12[CH2:32][CH2:31][C@H:30]3[C@@H:20]([CH2:21][CH:22]=[C:23]4[C@:28]3([CH3:29])[CH2:27][CH2:26][C@H:25]([OH:33])[CH2:24]4)[C@@H:19]1[CH2:18][CH2:17][O:16]2.CC(C)=O>O>[CH3:14][C@:15]12[CH2:32][CH2:31][C@H:30]3[C@@H:20]([CH2:21][CH2:22][C:23]4[C@:28]3([CH3:29])[CH2:27][CH2:26][C:25](=[O:33])[CH:24]=4)[C@@H:19]1[CH2:18][CH2:17][O:16]2

Participants

5

Reactant 3

HCID 180AcetoneHCID 67684023HCID 67684023, compoundHCID 131709961Jones' reagent

Product 1

HCID 53660110HCID 53660110, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.2 ml of Jones reagent was added dropwise at 0° C. to a mixture of 203 mg of 17-oxaandrost-5-en-3β-ol and 20 ml of acetone, and the mixture was stirred for 20 minutes. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extract was washed with 5% aqueous sodium bicarbonate solution and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled out, and the resultant 17-oxaandrost-5-en-3-one was dissolved in 10 ml of acetone. After addition of 0.01 ml of concentrated sulfuric acid, the reaction mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extract was washed with 5% aqueous sodium bicarbonate solution and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled out, and the resultant product was purified by TLC [developing solvent; chloroform: acetone (9:1)] to obtain 102 mg of 17-oxaandrost-4-en-3-one.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with 5% aqueous sodium bicarbonate solution and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out
  5. dissolutionthe resultant 17-oxaandrost-5-en-3-one was dissolved in 10 ml of acetone
  6. additionAfter addition of 0.01 ml of concentrated sulfuric acid
  7. stirringthe reaction mixture was stirred at room temperature for 2 hours
  8. additionWater was added to the reaction mixture
  9. extractionthe product was extracted with ethyl acetate
  10. washThe extract was washed with 5% aqueous sodium bicarbonate solution and saturated saline
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled out
  13. customthe resultant product was purified by TLC [developing solvent; chloroform: acetone (9:1)]

Sources & evidence

ORD record
ord-48616d522c0545ebaec615bb45a94465
Source dataset
uspto-grants-1996_05
Patent number
US05519051

Reaction notes

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