Potassium Carbonate → Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate

HRID 2412767Notes

Reaction equation

HRID 2412767 reaction equation
[C:1]([O:9][CH2:10][CH2:11]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:13][N:14]=[C:15]([C:21](=[O:23])[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:9][CH2:10][CH2:11][O:13][N:14]=[C:15]([C:21](=[O:23])[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5230902-Bromoethyl BenzoateHCID 178472877HCID 178472877, compound

Product 1

HCID 53765835Ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoethyl benzoate (27.5 g.) was added dropwise to a stirred mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer) (15.7 g.), potassium carbonate (20.7 g.) and N,N-dimethylformamide (25 ml.) under ice cooling over 10 minutes, and stirred at ambient temperature for 4 hours. The resultant mixture was filtred and washed with acetone. The filtrate and washings were combined and concentrated in vacuo. After adding water (100 ml.) to the residue, the solution was extracted with methylene chloride three times. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give ethyl 2-(2-benzoyloxyethoxyimino)-3-oxobutyrate (syn isomer) (28 g.).

Workup

  1. washwashed with acetone
  2. concentrationconcentrated in vacuo
  3. additionAfter adding water (100 ml.) to the residue
  4. extractionthe solution was extracted with methylene chloride three times
  5. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95b1297941494ae3a1144a87fd981970
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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