Imidazole → HCID 22097613, compound

HRID 964581Notes

Reaction equation

HRID 964581 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 4-bromobutyric acid benzyl ester (23.7 g), imidazole (8.1 g), potassium carbonate (14.0 g) and acetone (400 ml) was stirred under refluxing conditions for 6 hours. After the reaction mixture was cooled to room temperature, the insoluble solid was filtered off, the filtrate was concentrated. The residual oily substance was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (20:1, v/v) to yield 4-(1-imidazolyl)butyric acid benzyl ester (7.3 g, 33%) as an oily substance.

Workup

  1. filtrationthe insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. washeluted with ethyl acetate-methanol (20:1

Sources & evidence

ORD record
ord-3ed45cadc4b34ceba705c957520c258a
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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