Imidazole → 1-(1H-imidazol-1-yl)-3-methyl-2-butanol
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 16 h
- concentrationThe mixture was concentrated
- 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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