tert-Butyldimethylsilyl chloride → Tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane
Reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:18])[CH:16]=[CH2:17])=[CH:10][CH:9]=1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([Si:23]([O:18][C:15](=[CH:14][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=1)[CH:16]=[CH2:17])([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 104 mL (104.0 mmol, 1.2 equiv.) of a 1.0M solution of potassium tert-butoxide in THF and 100 mL dry THF under nitrogen atmosphere at −78° C. was added a solution of 14.2 g (86.6 mmol, 1 equiv.) of 1-(4-fluorophenyl)but-3-en-2-one (step B) and 13.0 g (86.6 mmol) tert-butylchlorodimethylsilane in 100 mL dry THF. The reaction mixture was stirred at −78° C. for 6 hr and at RT for 6 hr then quenched by the addition of 50 mL water. The resulting mixture was warmed to RT, diluted with 150 mL hexanes, transferred to a separatory funnel and the organic layer separated. The organic layer was washed with 50 mL brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under vacuum to give 20.5 g of the crude title compounds which were used without further purification. 1H-NMR (CDCl3): δ: 7.52 (2 H, m), 6.98 (2 H, m), 6.33 (1 H, dd, J1=13.2 Hz, J2=8.5 Hz), 5.97 (1 H, s), 5.52 (1 H, d, J=13.2 Hz), 5.17 (1 H, d, J=8.5 Hz).
Workup
- customthen quenched by the addition of 50 mL water
- temperatureThe resulting mixture was warmed to RT
- additiondiluted with 150 mL hexanes
- customtransferred to a separatory funnel
- customthe organic layer separated
- washThe organic layer was washed with 50 mL brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent evaporated under vacuum
Sources & evidence
- ORD record
- ord-4465382243e64ea390b1737171413acc
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345083B2
Reaction notes
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