Sodium hydride → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]=[O:9].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl>O>[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]=[O:9]Participants
Procedure
An oily suspension of 20.8 g sodium hydride in mineral oil (50%, 0.52 mol) was washed mineral oil free by stirring with hexane 3-times and suspended in 400 ml DMF. Under stirring at ambient temperature 50.0 g (0.520 mol) imidazole-2-carbaldehyde was added to the suspension. After 1.5 h, 101 ml (0.572 mol) 2-(trimethylsilanyl)ethoxymethyl chloride was added and the reaction was stirred a further hour. Then excess water was added to the suspension and the reaction mixture was extracted three times with ethyl acetate. The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The raw material was then purified by column chromatography (DCM) to yield 85.0 g (0.376 mol) of the SEM-protected imidazole-2-carbaldehyde.
Workup
- washwas washed mineral oil free
- additionwas added to the suspension
- stirringthe reaction was stirred a further hour
- extractionthe reaction mixture was extracted three times with ethyl acetate
- dry with materialThe organic phase was dried over Na2SO4
- customthe solvent was evaporated off under reduced pressure
- customThe raw material was then purified by column chromatography (DCM)
Sources & evidence
- ORD record
- ord-cb578041c017468fb81f18a570d43d8a
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376432B2
Reaction notes
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