Potassium Carbonate → 3-Chloro-5-ethynylpyridine

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Reaction Steps

Add potassium carbonate (4.35 g, 31.5 mmol) to a solution of 3-chloro-5-trimethylsilanylethynyl-pyridine (5.51 g, 26.3 mmol), (prepared as described in PREPARATION 26), in methanol (120 mL) and stir for 2 h. Concentrate, add water (150 mL), and extract with diethyl ether (2×100 mL). Wash the organic phase with an aqueous saturated solution of sodium chloride (100 mL), dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes to give the title compound as a pale yellow solid (1.9 g, 52%).

Provenance & Evidence