[OH-].[K+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:16][CH3:17])=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:9]=1>O.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:16][CH3:17])=[C:8]([C:10]#[CH:11])[CH:9]=1Add a solution of potassium hydroxide (3.28 g, 58.5 mmol) in water (30 mL) dropwise over 25 minutes to a stirred solution of (5-chloro-2-methoxy-phenylethynyl)-trimethylsilane (13.7 g, 57.4 mmol) in methanol (275 mL) and stir at room temperature for 2 hours. Concentrate, add brine to residue, and extract with EtOAc (×2). Dry organic layer over MgSO4 and concentrate to get 13 g of a black oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford the title compound (8.98 g, 94%).
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