Water → Methyl 2-benzyloxyiminoacetoacetate

HRID 1069197Notes

Reaction equation

HRID 1069197 reaction equation
[OH:1][N:2]=[C:3]([C:8]([CH3:10])=[O:9])[C:4]([O:6][CH3:7])=[O:5].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:11]([O:1][N:2]=[C:3]([C:8]([CH3:10])=[O:9])[C:4]([O:6][CH3:7])=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178501737HCID 178501737, compound

Product 1

HCID 53919435Methyl 2-benzyloxyiminoacetoacetateYield 77.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.0 g (103 mmol) of methyl 2-hydroxyiminoacetoacetate in 200 ml of acetone, 14.4 g (113 mmol) of benzyl chloride and 21.4 g (155 mmol) of potassium carbonate were added and the mixture was heated under reflux for 15 hours. The reaction mixture was combined with 200 ml of water and extracted three times with 200 ml of diethylether. After washing with water and a saturated aqueous sodium chloride followed by drying over with anhydrous magnesium sulfate, the solvent was distilled off. The residue thus obtained was purified by a column chromatography on a silica gel (n-hexane/ethyl acetate) to obtain 18.7 g (yield: 77%) of methyl 2-benzyloxyiminoacetoacetate as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted three times with 200 ml of diethylether
  4. washAfter washing with water
  5. dry with materialby drying over with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue thus obtained
  8. customwas purified by a column chromatography on a silica gel (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6615ddeceb0a4be4a699e8ede4753b77
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Reaction notes

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