Imidazole → 1-(1H-imidazol-1-yl)-3-methyl-2-butanol

HRID 496434Notes

Reaction equation

HRID 496434 reaction equation
[CH:1]([CH:4]1[CH2:6][O:5]1)([CH3:3])[CH3:2].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1>C(#N)C>[N:7]1([CH2:6][CH:4]([OH:5])[CH:1]([CH3:3])[CH3:2])[CH:11]=[CH:10][N:9]=[CH:8]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 1026181,2-Epoxy-3-methylbutane

Product 1

HCID 223247001-(1H-imidazol-1-yl)-3-methyl-2-butanolYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-isopropyloxirane (2.28 g, 26 mmol) and imidazole (1.80 g, 26 mmol) in acetonitrile (25 mL) was stirred at reflux for 16 h. The mixture was concentrated, and the residue was purified by flash column chromatography (SiO2, CH2Cl2-methanol-ammonium hydroxide 80:20:1) to give 1-(1H-imidazol-1-yl)-3-methyl-2-butanol as a yellow oil, 1.88 g, 46% yield. NMR spectrum was consistent with structure. MS EI: M+• 154.1103 (M+• −154.1106). 4. 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by flash column chromatography (SiO2, CH2Cl2-methanol-ammonium hydroxide 80:20:1)

Sources & evidence

ORD record
ord-a76fd5db663444ac9ce001ed4653921c
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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