Acetone → Unii-WY74vse2QY

HRID 49525Notes

Reaction equation

HRID 49525 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)=[O:9])=[O:2].CC(C)=[O:27].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>O>[CH3:24][O:23][C:6]1[CH:5]=[CH:4][C:3]([C:1]([OH:27])=[O:2])=[CH:22][C:7]=1[C:8](=[O:9])[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 120946615-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamideHCID 131709961Jones' reagent2×

Product 1

HCID 9798618Unii-WY74vse2QY

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 500 mg of 5-formyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide were added 20 ml of acetone and 0.5 ml of Jones reagent under cooling with ice, and the mixture was stirred for 25 minutes. Then, 0.2 ml of Jones reagent were added further and the mixture was stirred for 35 minutes. To the reaction mixture were added 100 ml of water, which was extracted (100 ml×2) with methylene chloride (small quantity of acetone was added). After washed with 50 ml of saturated brine, the organic layer was dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel, methylene chloride:methanol=100:1, quantity of methanol was increased gradually), then recrystallized from hexane-acetone to obtain 270 mg of aimed product as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 35 minutes
  3. extractionwas extracted (100 ml×2) with methylene chloride (small quantity of acetone was added)
  4. washAfter washed with 50 ml of saturated brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. distillationSolvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customwas purified by means of column chromatography (silica gel, methylene chloride
  9. temperaturemethanol=100:1, quantity of methanol was increased gradually),
  10. customthen recrystallized from hexane-acetone

Sources & evidence

ORD record
ord-349e247835354eada9f08dcbb4d69996
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Reaction notes

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