Imidazole → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13]Cl>CN(C)C=O>[CH3:8][Si:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][O:12][CH2:13][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under an argon atmosphere, a dimethylformamide (500 mL) suspension of sodium hydride (60%, 18.9 g) was ice-cooled and then imidazole (30.9 g) was added so as to prevent an inner temperature from rising to 5° C. or higher. The reaction solution was stirred at 0° C. for 45 minutes. To the reaction solution, 2-(trimethylsilyl)ethoxymethyl chloride (72.4 g) was added dropwise. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, ice water (200 mL) was added. The aqueous layer was extracted twice with a solution (n-hexane:ethyl acetate=1:1 (200 mL)). The combined organic layer was washed with saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate by filtration, the filtrate was concentrated to obtain the title compound (116 g) having the following physical properties.
Workup
- temperaturecooled
- customfrom rising to 5° C.
- stirringThe reaction solution was stirred at room temperature for 14 hours
- extractionThe aqueous layer was extracted twice with a solution (n-hexane:ethyl acetate=1:1 (200 mL))
- washThe combined organic layer was washed with saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customAfter removing anhydrous magnesium sulfate
- filtrationby filtration
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-39f9eb6a55bb409d8e5b46bd149e8ffa
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318931B2
Reaction notes
Loading…