Acetone → HCID 53837207, compound

HRID 1637010Notes

Reaction equation

HRID 1637010 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][OH:17])[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2].[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.CC(C)=O>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][O:17][CH3:18])[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 73604849HCID 73604849, compound

Product 1

HCID 53837207HCID 53837207, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-hydroxyiminoacetamide (253 mg, E/Z≠65/35), potassium carbonate (177 mg), 95% dimethyl sulfate (148 mg) and acetone (4.0 ml) was stirred at room temperature for 4 hours. A few pieces of ice were added, and the mixture was stirred for 20 minutes. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product. The crude product was purified by column chromatography on silica gel (ethyl acetate/hexane=2/1) to obtain the title compound (194 mg, E/Z≠79/21, yield: 72.4%).

Workup

  1. additionA few pieces of ice were added
  2. stirringthe mixture was stirred for 20 minutes
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent under reduced pressure
  6. customgave the crude product
  7. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-6cb6a374dcab473594c4a29cd8257828
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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