Imidazole → HCID 53673103, compound

HRID 1728413Notes

Reaction equation

HRID 1728413 reaction equation
[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[NH:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1>[Pd]>[N:6]1([C:5]([CH2:2][CH:3]=[CH:4][CH2:13][OH:14])=[O:1])[CH:10]=[CH:9][N:8]=[CH:7]1.[N:6]1([C:2]([CH:12]([CH2:13][OH:14])[CH:11]=[CH2:15])=[O:1])[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

6

Reactant 3

HCID 795Imidazole2×HCID 8028TetrahydrofuranHCID 13586Vinyloxirane2×

Product 2

HCID 53673103HCID 53673103, compoundYield 95%HCID 54181380HCID 54181380, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Reaction of 3,4-epoxy-1-butene and imidazole 1.95 g (0.0286 moles) of imidazole and 2.0 g (0.0286 moles) of 3,4-epoxy-1-butene were dissolved in 25 ml of THF. 0.83 g of the polymer-bound palladium(0) catalyst of Example 2 was then added to the reaction mixture. The reaction mixture was stirred at room temperature for 24 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure. The residue was distilled. The reaction Yielded about 95% 4-(1-imidazoYl)-2-buten-1-ol (1,4 adduct) and less than 5% 3-(1-imidazoyl)-1-buten-4-ol (1,2 adduct). The combined yield of products was 63%.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure
  3. distillationThe residue was distilled

Sources & evidence

ORD record
ord-dfe18114c91d404484eb63a60e25a99b
Source dataset
uspto-grants-1994_07
Patent number
US05326873

Reaction notes

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