Imidazole → HCID 22097613, compound

HRID 862660Notes

Reaction equation

HRID 862660 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:15]1([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 3832489Benzyl 4-bromobutanoate

Product 1

HCID 22097613HCID 22097613, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzyl 4-bromobutyrate (23.7 g), imidazole (8.1 g), potassium carbonate (14.0 g) and acetone (400 ml) was stirred under reflux for 6 hours. After cooling the mixture to room temperature, the insoluble material was filtered off, and the filtrate was concentrated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate/methanol (20/1, v/v) gave benzyl 4-(1-imidazolyl)butyrate (7.3 g, 33%) as an oil.

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. washThe fractions eluted with ethyl acetate/methanol (20/1

Sources & evidence

ORD record
ord-05a5c7de65b0473ba1240975da31d788
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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