[C:1]([O:4][C:5]1[C:6]([C:11]#[C:12][Si](C)(C)C)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:4][C:5]1[C:6]([C:11]#[CH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]To a solution of 2-((trimethylsilyl)ethynyl)pyridin-3-yl acetate (9.5 g, 41 mmol) in THF (200 mL) was added water (25 ml). The reaction was cooled to 0° C. and TBAF (1M, 45 ml, 45 mmol) was added. The mixture warmed to ambient temperature and stirred for 1 hour. Water (100 mL) was added and the volume was reduced by half. The product was extracted into ether (3×100 mL), washed with brine and dried over MgSO4. The solution was concentrated in vacuo to afford 2-ethynylpyridin-3-yl acetate (5.5 g, 34 mmol) as a light brown oil.
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