Acetone → HCID 53713376, compound

HRID 440439Notes

Reaction equation

HRID 440439 reaction equation
CC(C)=[O:3].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][O:17][CH2:16]2.CC(C)=O.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:14][C@:15]12[CH2:32][CH2:31][C@H:30]3[C@@H:20]([CH2:21][C:22](=[O:3])[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][O:17][CH2:16]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 54086454HCID 54086454, compoundHCID 131709961Jones' reagent

Product 1

HCID 53713376HCID 53713376, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

30 μl of Jones reagent was added dropwise at 0° C. to a mixture of 10 mg of 16-oxaandrost-5-en-3β-ol and 0.5 ml of acetone, and the mixture was stirred at room temperature for 30 minutes. 2-propanol and 5% aqueous sodium bicarbonate solution were added to the reaction mixture and the insoluble matters were removed by filtration. The filtrate was concentrated under reduced pressure, water was added, and the product was extracted with ethyl acetate. The extract was washed with 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 3 mg of 16-oxaandrost-4-ene-3,6-dione.

Workup

  1. customthe insoluble matters were removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate
  5. washThe extract was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled out
  8. customthe resultant crude product was purified by TLC [developing solvent; chloroform acetone (19:1)]

Sources & evidence

ORD record
ord-a86f7e53abc743b3a4cde2317612a0db
Source dataset
uspto-grants-1996_05
Patent number
US05519051

Reaction notes

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