Potassium Carbonate → ethyl (2-formyl-1H-imidazol-1-yl)acetate

HRID 856791Notes

Reaction equation

HRID 856791 reaction equation
[CH:1]([C:3]1[NH:4][CH:5]=[CH:6][N:7]=1)=[O:2].[C:8]([O:11][CH2:12][CH2:13]Br)(=[O:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([C:3]1[N:4]([CH2:9][C:8]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][N:7]=1)=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 62222097ethyl (2-formyl-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-formylimidazole (5.16 g), bromoethyl acetate (7.1 ml) and potassium carbonate (11.1 g) in. DMF (50 ml) was stirred for 20 hours at 60° C. The insolubles were removed by filtration, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:1), to give ethyl (2-formyl-1H-imidazol-1-yl)acetate (1.10 g) as pale yellow oil.

Workup

  1. customThe insolubles were removed by filtration, water
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was separated
  8. custompurified by column chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-68b93a7fe6e043de8a1542c6384c7cbb
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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