[Br:1][C:2]([F:16])([F:15])[C:3]#[C:4][Si](C(C)C)(C(C)C)C(C)C.[CH3:17][C:18]([CH3:22])([CH3:21])[CH:19]=[O:20]>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Br:1][C:2]([F:15])([F:16])[C:3]#[C:4][CH:19]([OH:20])[C:18]([CH3:22])([CH3:21])[CH3:17]To a solution of (3-bromo-3,3-difluoro-prop-1-ynyl)-triisopropyl-silane (156 mg, 0.5 mmol) and 2,2-dimethyl-propionaldehyde (52 mg, 0.6 mmol) in THF (5 mL), TBAF (1M, 0.75 mL) was added dropwise at −90° C. After the addition was completed, the reaction mixture was stirred for 0.5 hour and quenched saturated aq. NH4Cl. The mixture was extracted with ether (20 mL×3) and washed with water (20 mL×2). After drying over Na2SO4 the solvent was removed and the product was purified by silica gel chromatography (AcOEt:hexane=1:20) to afford the title compound as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 4.08-4.09 (m, 1H), 1.83 (d, J=6.0 Hz, 1H), 0.965 (s, 9H).
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