Imidazole → HCID 53725360, compound

HRID 638616Notes

Reaction equation

HRID 638616 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[Br:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[CH:17][C:18]=1[CH2:19]Br.C1OCCOCCOCCOCCOCCOC1>CCOCC.O>[Br:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[CH:17][C:18]=1[CH2:19][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 54409993HCID 54409993, compound

Product 1

HCID 53725360HCID 53725360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of imidazole (0.25 g, 3.67 mmol), potassium tert-butoxide (0.42 g, 3.75 mmol), ethyl 3-(3-bromo-4-bromomethylphenyl)prop-2-enoate (1.29 g, 3.7 mmol) and 18-crown-6 (0.1 g) in dry ether was stirred at room temperature for 72 h. Water (5 ml) was then added, and the aqueous layer was extracted with ether (3×50 ml). The ether solutions were combined, dried (MgSO4) and then concentrated to afford a pale yellow oil. The oil was `flash` chromatographed using chloroform/methanol 9:1 as eluant. The product fractions were combined, dried (MgSO4) and concentrated to afford ethyl 3-[3-bromo-4-(imidazol-1-ylmethyl)phenyl]prop-2-enoate as a white solid. NMR data was consistent with the assigned structure.

Workup

  1. extractionthe aqueous layer was extracted with ether (3×50 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a pale yellow oil
  5. customchromatographed
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4560867ade6d4a85a084fa7d0bb9d84b
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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