Butyl iodide → Ethyl 2-(butoxyimino)-3-oxobutanoate

HRID 1650428Notes

Reaction equation

HRID 1650428 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH3:4].[OH:6][N:7]=[C:8]([C:14](=[O:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:6][N:7]=[C:8]([C:14](=[O:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 53974956Ethyl 2-(butoxyimino)-3-oxobutanoateYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

n-Butyl iodide (46.9 g.) was added dropwise to a stirred suspension of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 40 g.), potassium carbonate (52.7 g.) and acetone (200 ml.) under ice-cooling over 5 minutes, and stirred at room temperature for 4 hours. The resultant solution was filtered, and washed with acetone. The filtrate and washing solution were combined together and concentrated in vacuo. After adding water (300 ml.) to the residue, the solution was extracted with methylene chloride three times. The solution was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-n-butoxyimino-3-oxobutyrate (syn isomer, 48.8 g.), oil.

Workup

  1. temperaturecooling over 5 minutes
  2. filtrationThe resultant solution was filtered
  3. washwashed with acetone
  4. washThe filtrate and washing solution
  5. concentrationconcentrated in vacuo
  6. additionAfter adding water (300 ml.) to the residue
  7. extractionthe solution was extracted with methylene chloride three times
  8. washThe solution was washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec3e26deadaf401ab0d7c550c2385de3
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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