p-Toluenesulfonic acid monohydrate → (5-Methanesulfonyl-pyridin-3-yl)-propynoic acid ethyl ester

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Reaction Steps

p-Toluenesulfonic acid monohydrate (1.39 g, 0.73 mmol) was added to a solution of 3-methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine (1.20 g, 3.70 mmol) in toluene (40 mL). After stirring overnight at room temperature, the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (0.55 g, 53% yield) as a white solid. 1H NMR (CDCl3) δ 9.17 (d, 1H, J=2.4 Hz), 9.03 (d, 1H, J=2.0), 8.40 (t, 1H, J=2.0 Hz), 4.35 (q, 6H, J=8.0), 3.14 (s, 3H), 1.38 (t, 9H, J=8.0).

Provenance & Evidence