Isopropanol → HCID 54317930, compound

HRID 440437Notes

Reaction equation

HRID 440437 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][O:10][C:11]2=[O:21])[CH2:3]1.CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][C:5](=[O:24])[C:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH:3]=4)[C@@H:8]1[CH2:9][O:10][C:11]2=[O:21]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 54167320HCID 54167320, compoundHCID 131709961Jones' reagent

Product 1

HCID 54317930HCID 54317930, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

53 mg of 3β-hydroxy-16-oxaandrost-5-en-17-one was dissolved in 2.4 ml of acetone and the solution was cooled with ice. 60 μl of Jones reagent was added dropwise to this solution under ice cooling and stirring, and the mixture was stirred for 15 minutes. 2-propanol was added to the reaction mixture and the insoluble matters were removed by filtration. The filtrate was concentrated, water was added and the mixture was extracted with ethyl acetate. The extract was washed with 5% aqueous sodium bicarbonate solution, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled out, and the resultant crude product was purified by TLC [developing solvent; chloroform: acetone (19:1)] to obtain 9 mg of 16-oxaandrost-4-ene-3,6,17-trione.

Workup

  1. temperaturethe solution was cooled with ice
  2. stirringthe mixture was stirred for 15 minutes
  3. customthe insoluble matters were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with 5% aqueous sodium bicarbonate solution, water and saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled out
  10. customthe resultant crude product was purified by TLC [developing solvent; chloroform: acetone (19:1)]

Sources & evidence

ORD record
ord-7b5a0bbc334e4ffe9342289b95f1c0a0
Source dataset
uspto-grants-1996_05
Patent number
US05519051

Reaction notes

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