Water → Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate

HRID 261977Notes

Reaction equation

HRID 261977 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([C:10](=[N:16][OH:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH3:8].S(OC)(OC)(=O)=O.O>CC(C)=O>[C:7]([C:10](=[N:16][O:17][CH3:1])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoateYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

234 g of potassium carbonate were added at 10° C. under a nitrogen atmosphere to a mixture of 180 g of raw ethyl 2-acetyl-2-hydroxyiminoacetate in 900 ml of pure acetone and then 103 ml of dimethyl sulfate were added thereto. The mixture was stirred at room temperature for 3 hours and was then poured into ice and 4 liters of water were added. The mixture was extracted with methylene chloride and the extracts were washed with water, dried and distilled to dryness to obtain 185 g of ethyl 2-acetyl-2-methoxyiminoacetate.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe extracts were washed with water
  4. customdried
  5. distillationdistilled to dryness

Sources & evidence

ORD record
ord-5a8aa804055e4581b5ae30abbe60842e
Source dataset
uspto-grants-1979_05
Patent number
US04152432

Reaction notes

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