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

HRID 1277636Notes

Reaction equation

HRID 1277636 reaction equation
[O:1]=[C:2]([CH3:11])[C:3](=[N:9][OH:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CO.S(OC)(O[CH3:18])(=O)=O>C(=O)([O-])[O-].[Na+].[Na+].O>[O:1]=[C:2]([CH3:11])[C:3](=[N:9][O:10][CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 178472877HCID 178472877, compound

Product 1

HCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoateYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

In a solution of 13.3 g of sodium carbonate in 120 ml of water is dissolved 10 g of ethyl 3-oxo-2-hydroxyiminobutyrate, followed by addition of 30 ml of methanol. The mixture is cooled with ice and, under stirring, 15.8 g of dimethyl sulfate is added dropwise over a period of 3 minutes. After the dropwise addition has been completed, the ice-bath is removed and the mixture is stirred at room temperature for 40 minutes. The reaction mixture (pH 8 or higher) is extracted twice with ethyl acetate and the extracts are pooled, washed with water and dried. The solvent is then evaporated off under reduced pressure and the residue is subjected to distillation under reduced pressure. By the above procedure is obtained 9 g of ethyl 3-oxo-2-methoxyiminobutyrate as a pale-yellow oil boiling at 56°-61° C./0.3-0.4 mmHg.

Workup

  1. temperatureThe mixture is cooled with ice
  2. additionAfter the dropwise addition
  3. customthe ice-bath is removed
  4. stirringthe mixture is stirred at room temperature for 40 minutes
  5. extractionThe reaction mixture (pH 8 or higher) is extracted twice with ethyl acetate
  6. washwashed with water
  7. customdried
  8. customThe solvent is then evaporated off under reduced pressure
  9. distillationthe residue is subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-3a215aa01e6c4f53bcba7b8e7c4c118f
Source dataset
uspto-grants-1981_07
Patent number
US04278671

Reaction notes

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