Hexane → Chloromethyl[bis(4-fluorophenyl)](1-hexynyl)silane
Reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.CCCCCC.[F:18][C:19]1[CH:24]=[CH:23][C:22]([Si:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)(Cl)[CH2:26][Cl:27])=[CH:21][CH:20]=1>O1CCCC1>[Cl:27][CH2:26][Si:25]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)([C:22]1[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=1)[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Procedure
A solution of 2.9 ml (0.024 mol) of 1-hexyne in 50 ml of tetrahydrofuran under nitrogen was cooled to -5° C. A solution of n-butyllithium in hexane (15 ml of 1.6 molar, 0.024 mol) was added dropwise, and the resulting solution was warmed to room temperature and stirred for 1.5 hours. The solution was then cooled to -65° C., and a solution of 6.0 g (0.0198 mol) of bis(4-fluorophenyl)chlorochloromethylsilane in 10 ml of THF was added dropwise. The reaction was warmed to room temperature and quenched by addition of saturated aqueous ammonium chloride. The solution was partitioned between water and ether, and the organic layer was separated, washed with brine and dried over magnesium sulfate. Removal of solvent gave the title compound as a clear colorless oil: nmr (CDCl3) 1.0 (3H, m), 1.5 (4H, m), 2.4 (2H, m), 3.2 (2H, s), 7.2 (4H, t, J= 9 Hz), 7.7 (4H, d of d, J=9, 6 Hz); ir (neat) 2180 cm-1.
Workup
- temperatureThe solution was then cooled to -65° C.
- temperatureThe reaction was warmed to room temperature
- customquenched by addition of saturated aqueous ammonium chloride
- customThe solution was partitioned between water and ether
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried over magnesium sulfate
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-c2776b6f5b26486eb8fcccc544e29e1f
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04530922
Reaction notes
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