1-Bromopentane → Ethyl 3-oxo-2-[(pentyloxy)imino]butanoate

HRID 1388460Notes

Reaction equation

HRID 1388460 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](Br)[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:18]([O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 53697317Ethyl 3-oxo-2-[(pentyloxy)imino]butanoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer) (40 g.) and potassium carbonate (52 g.) in dimethylformamide (200 ml.) was added pentyl bromide (37.9 g.) with stirring, and the mixture was stirred for 1.5 hours at ambient temperature. The insoluble material was collected by filtration and washed with dimethylformamide. The filtrate and the washings were combined together and evaporated to dryness under reduced pressure. To the residue was added water and the mixture was extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give an oil of ethyl 2-pentyloxyimino-3-oxobutyrate (syn isomer) (57.5 g.).

Workup

  1. stirringthe mixture was stirred for 1.5 hours at ambient temperature
  2. filtrationThe insoluble material was collected by filtration
  3. washwashed with dimethylformamide
  4. customevaporated to dryness under reduced pressure
  5. additionTo the residue was added water
  6. extractionthe mixture was extracted with chloroform
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee8ba0b893724361bd8cc23559062f1a
Source dataset
uspto-grants-1984_02
Patent number
US04431643

Reaction notes

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