OS(O)(=O)=O.[CH2:6]([C:8]1[CH:9]=[C:10]([C:15]#[C:16][Si](C)(C)C)[CH:11]=[CH:12][C:13]=1[F:14])[CH3:7].[O:21]1CCCC1>O.[Hg]=O>[CH2:6]([C:8]1[CH:9]=[C:10]([C:15](=[O:21])[CH3:16])[CH:11]=[CH:12][C:13]=1[F:14])[CH3:7]To a stirred solution of H2SO4 (0.25 mL) in H2O (3 mL), HgO (154 mg, 0.712 mmol) was added. Another portion of H2SO4 (0.5 mL) was added so that all of the mercury oxide dissolved. Then the mixture was warmed to 60° C. and (3-ethyl-4-fluoro-phenylethynyl)-trimethyl-silane (1.57 g, 7.12 mmol) was added with tetrahydrofuran (2 mL) during 20 minutes. After the addition, the mixture was stirred for an additional 30 minutes and then cooled and extracted with ether. The extract was passed through a celite pad, washed with saturated brine and dried (Na2SO4). Removal of solvent on a rotary evaporator gave a brown oil, which was chromatographed (25%, dichloromethane/hexanes) to give a yellow oil. 404 mg, 34%.
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