Triethylamine → Triisopropyl{[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1.C(N(CC)CC)C.FC(F)(F)S(O[Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])(=O)=O.[Cl-].[NH4+]>ClCCl>[CH:31]([Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:16][C:13]1[CH2:12][CH2:11][CH:10]([C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:15][CH:14]=1)([CH3:33])[CH3:32]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A three-neck flask (1 L) containing a stirred solution of 4-(2,4,5-trifluorophenyl)cyclohexanone (15.8 g) in dichloromethane (160 mL) under a nitrogen atmosphere was cooled to 0° C. and then treated with triethylamine (22 mL) followed by triisopropylsilyl trifluoromethanesulfonate (25.4 g) while maintaining the temperature below 5° C. The solution was stirred at 0° for 30 min and then allowed to rise to ambient temperature over a period of 0.5 h. It was then treated with saturated aqueous ammonium chloride solution. The organic layer was separated, dried over anhydrous magnesium sulfate and evaporated. The crude product was chromatographed (silica gel, 3% ether in hexane) to yield the title compound.
Workup
- temperaturewhile maintaining the temperature below 5° C
- waitto rise to ambient temperature over a period of 0.5 h
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customThe crude product was chromatographed (silica gel, 3% ether in hexane)
Sources & evidence
- ORD record
- ord-73796fe077a94abb8e44de766e7bcc96
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855206B2
Reaction notes
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