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

HRID 894448Notes

Reaction equation

HRID 894448 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 95.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.1 kg of potassium carbonate were added at 20°-25° C. to a mixture of 4.69 kg of ethyl 2-acetyl-2-hydroxyiminoacetate (equal to 4.21 kg of pure product) in 21 liters of anhydrous pure acetone and after stirring the suspension for 10 minutes, 3.72 kg of dimethyl sulfate were added at 20°-25° C. The mixture was poured into 126 liters of demineralized water and was extracted 4 times with 5 liters and then with 2 liters of methylene chloride. The combined extracts were washed with 10 liters of demineralized water, were dried and vacuum filtered. The filter was rinsed with 2 liters of methylene chloride and the filtrate was evaporated to dryness under reduced pressure to obtain 4.88 kg of ethyl 2-acetyl-2-meth-oxyiminoacetate with an Rf=0.7 (thin layer chromatography-9-1-methylene chloride-ethyl acetate eluant). The product was identical to that product in Step A of Example 3.

Workup

  1. extractionwas extracted 4 times with 5 liters
  2. washThe combined extracts were washed with 10 liters of demineralized water
  3. customwere dried
  4. filtrationvacuum filtered
  5. washThe filter was rinsed with 2 liters of methylene chloride
  6. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8453038028b742869cf3ca9f3201677d
Source dataset
uspto-grants-1981_08
Patent number
US04283396

Reaction notes

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