Oxazole → 2-(Tris(propan-2-yl)silyl)-1,3-oxazole
Reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CCCCCC.C([Li])CCC.O([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])S(C(F)(F)F)(=O)=O>C1COCC1>[CH:26]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[C:2]1[O:1][CH:5]=[CH:4][N:3]=1)([CH3:28])[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of oxazole (2.1 g) in THF (90 mL) was added dropwise n-butyllithium hexane solution (1.6M, 19.7 mL) at −78° C. The reaction mixture was stirred at 0° C. for 10 min under nitrogen atmosphere, and triisopropylsilyl triflate (8.5 mL) was added thereto. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (6.7 g).
Workup
- stirringThe reaction mixture was stirred at room temperature for 2 hr
- customthe solvent was evaporated under reduced pressure
- additionTo the residue was added ethyl acetate
- washthe mixture was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-cf558105b69d492692ea03086445a860
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296746B2
Reaction notes
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