Potassium Carbonate → Ethyl 3-oxo-2-(propoxyimino)butanoate

HRID 1650418Notes

Reaction equation

HRID 1650418 reaction equation
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH2:19][CH3:20]>CC(C)=O>[O:11]=[C:9]([CH3:10])[C:3](=[N:2][O:1][CH2:18][CH2:19][CH3:20])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178472877HCID 178472877, compound

Product 1

HCID 54491732Ethyl 3-oxo-2-(propoxyimino)butanoateYield 81.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 15 g.) and potassium carbonate (19.8 g.) in acetone (75 ml.) was added dropwise propyliodide (16.2 g.) with stirring, and the mixture was stirred at ambient temperature for 1,5 hours. The insoluble substance was collected by filtration and washed with acetone. The washings and the filtrate were combined and evaporated to dryness under reduced pressure. To the resultant residue was added water and the aqueous solution was extracted twice with chloroform. The extract was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, and then evaporated to dryness under reduced pressure to give ethyl 3-oxo-2-propoxyiminobutyrate (syn isomer, 15.4 g.), oil.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1,5 hours
  2. filtrationThe insoluble substance was collected by filtration
  3. washwashed with acetone
  4. customevaporated to dryness under reduced pressure
  5. additionTo the resultant residue was added water
  6. extractionthe aqueous solution was extracted twice with chloroform
  7. washThe extract was washed with an aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-dbc9632800c74f2792ad1dca8e8854f6
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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