[F:1][C:2]([F:19])([C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:4][Si:5](Cl)(Cl)Cl.[CH:20]([Li])([CH3:22])[CH3:21].[C:24]([Mg]Br)#[CH:25].[CH2:28]1[CH2:32]OC[CH2:29]1>>[F:1][C:2]([F:19])([C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:4][Si:5]([C:24]#[CH:25])([CH:28]([CH3:32])[CH3:29])[CH:20]([CH3:22])[CH3:21]To an oven-dried 250-mL round bottom flask was added 3,3,4,4,5,5,6,6,6-nonafluorohexyltrichlorosilane (4.52 g, 11.9 mmol) and anhydrous THF (20 mL). Isopropyllithium (34 mL, 24 mmol, 0.7 M in pentane) was added dropwise over 1 hr, then stirring was continued for 4 hr. Ethynylmagnesium bromide (32 mL, 16 mmol, 0.5 M in THF) was added slowly, then the reaction mixture was heated to 50° C. for 12 hr. The reaction was quenched with water and dilute sulfuric acid to dissolve the salts, then hexane was added and the organic layer was separated. The organic layer was washed with water (5×20 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum to yield the crude product mixture. Purification by silica chromatography with hexane as an eluant (Rf˜0.6 in hexane) yielded 1.8 g (4.6 mmol, 31%) of the desired product as a colorless liquid. Analysis of the colorless product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.2 (m, 2H), 1.1 (m, 14H), 0.8 (m, 2H).
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