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

HRID 1659762Notes

Reaction equation

HRID 1659762 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 filtered 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. filtrationThe resultant mixture was filtered
  2. washwashed with acetone
  3. concentrationconcentrated in vacuo
  4. additionAfter adding water (100 ml.) to the residue
  5. extractionthe solution was extracted with methylene chloride three times
  6. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efe3abe7b6454bfd98ecd545c88363a4
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

Loading…