Ethyl bromoacetate → HCID 86742069, compound

HRID 569762Notes

Reaction equation

HRID 569762 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9](C(=O)CC(OC)=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:22][C:23]([O:25]CC)=[O:24].[O:28]1CC[CH2:30][CH2:29]1>>[N:1]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:29](=[O:28])[CH2:30][CH2:22][C:23]([OH:25])=[O:24])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 13059430HCID 13059430, compound

Product 1

HCID 86742069HCID 86742069, compound

Procedure

A solution of methyl 4-(1H-imidazol-1-yl)-β-oxo-benzenepropanoate (6.1 g, 0.025 mol) in tetrahydrofuran (65 ml) is added slowly to a stirred suspension of 50% NaH (1.2 g, 0.025 mol) in tetrahydrofuran (20 ml) and the solution is stirred for one additional hour. Ethyl bromoacetate (4.5 g) is added followed by refluxing the mixture for seven to eight hours. The tetrahydrofuran is removed, the residue is treated with water, and the organic material is extracted with ether. The residue obtained after removal of the ether is hydrolysed by heating with 6N HCl for eight hours. The crude acid is finally crystallized from dimethylformamide to yield 3.3 g of the product 4-(1-imidazol-1-yl)-γ-oxobenzenebutanoic acid.

Workup

  1. temperatureby refluxing the mixture for seven to eight hours
  2. customThe tetrahydrofuran is removed
  3. additionthe residue is treated with water
  4. extractionthe organic material is extracted with ether
  5. customThe residue obtained
  6. customafter removal of the ether
  7. temperatureby heating with 6N HCl for eight hours
  8. customThe crude acid is finally crystallized from dimethylformamide

Sources & evidence

ORD record
ord-a558f9ce572e47d4ba210376a1fe338e
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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