Imidazole → 1-(1H-imidazol-1-yl)-2-butanol

HRID 496439Notes

Reaction equation

HRID 496439 reaction equation
[O:1]1[CH:3]([CH2:4][CH3:5])[CH2:2]1.[NH:6]1[CH:10]=[CH:9][N:8]=[CH:7]1>C(#N)C>[N:6]1([CH2:2][CH:3]([OH:1])[CH2:4][CH3:5])[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 78341,2-Epoxybutane

Product 1

HCID 223247611-(1H-imidazol-1-yl)-2-butanolYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,2-epoxybutane (2.0 mL, 23 mmol) and imidazole (2.37 g, 35 mmol) in acetonitrile (20 mL) was stirred at reflux for 24 h. The mixture was concentrated, taken up in water (30 mL) and extracted with ethyl acetate (9×10 mL). The combined extracts were dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, CH2Cl2-methanol-ammonium hydroxide 80:20:1) to give 1-(1H-imidazol-1-yl)-2-butanol (1.57 g, 48%) as a colorless oil. NMR spectrum was consistent with structure. MS EI: M+• 140.0948 (M+• 140.0950).

Workup

  1. temperatureat reflux for 24 h
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate (9×10 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2-methanol-ammonium hydroxide 80:20:1)

Sources & evidence

ORD record
ord-b045437a6c724a82bd983beed33c574c
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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