Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([F:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>C1COCC1>[Si:11]([O:10][CH2:9][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:26]=[O:27])[F:18])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of (2-(3-bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilane (example 39, step c) (1.8 g) in THF (36 mL) was cooled to −78° C. under an atmosphere of nitrogen and treated with butyllithium (1.8M in hexanes, 3.3 mL), added dropwise over 5 minutes. The solution was stirred at −78° C. for 30 minutes, treated with N,N-dimethylformamide (0.63 mL), stirred at −78° C. for a further 30 minutes, then removed from the cooling bath and allowed to warm to room temperature over 140 minutes. The solution was quenched by the addition of 10% aqueous ammonium chloride, and the resulting mixture was extracted twice with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 50% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 1.26 g.
Workup
- additionadded dropwise over 5 minutes
- stirringstirred at −78° C. for a further 30 minutes
- customremoved from the cooling bath
- temperatureto warm to room temperature over 140 minutes
- customThe solution was quenched by the addition of 10% aqueous ammonium chloride
- extractionthe resulting mixture was extracted twice with diethyl ether
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous magnesium sulphate
- custompurified by flash chromatography on silica
- washeluted with 50% dichloromethane in isohexane
Sources & evidence
- ORD record
- ord-70ccd8263d074370b4a469ecc1e30aac
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Linked notes
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