Water → 4-Chloro-2-ethynyl-1-methoxybenzene
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[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[CH:9])[CH:7]=1[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]#[CH:9])[CH:7]=1((5-chloro-2-methoxyphenyl)ethynyl)trimethylsilane (0.4 g, 1.7 mmol) was dissolved in MeOH (1 mL), K2CO3 (0.69 g, 5 mol) was added to it. Then the mixture was stirred at 25° C. for 1 hour, and added to H2O (50 mL). The mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4. After the combined organic layers were concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=10:1) to provide the product of 4-chloro-2-ethynyl-1-methoxybenzene (0.25 g, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 7.43 (s, 1H), 7.28˜7.29 (m, 1H), 6.81˜6.85 (m, 1H), 3.89 (s, 3H), 3.34 (s, 1H). MS (M+H)+: 167/169.
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