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

HRID 496437

Reaction equation

HRID 496437 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:2]1.[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1>C(#N)C>[N:8]1([CH2:2][CH:3]([OH:1])[CH2:4][CH2:5][CH2:6][CH3:7])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 150362-Butyloxirane

Product 1

HCID 205730271-(1H-imidazol-1-yl)-2-hexanolYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,2-epoxyhexane (2.0 mL, 17 mmol) and imidazole (1.08 g, 16 mmol) in acetonitrile (14 mL) was stirred at reflux for 19 h. The mixture was concentrated, taken up in 2.5 M aqueous hydrochloric acid (15 mL), washed with ethyl acetate (3×6 mL), basified with sodium carbonate and extracted with ethyl acetate (3×6 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-hexanol as a colorless oil, 1.68 g, 63% yield. NMR spectrum was consistent with structure. MS EI: M+• 168.1259 (M+• 168.1263).

Workup

  1. temperatureat reflux for 19 h
  2. concentrationThe mixture was concentrated
  3. washwashed with ethyl acetate (3×6 mL)
  4. extractionextracted with ethyl acetate (3×6 mL)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (SiO2, CH2Cl2-methanol-ammonium hydroxide 80:20:1)

Sources & evidence

ORD record
ord-018d6bb9cb0f47778c4e0263f11b5d54
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Linked notes

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