Attempted Preparation of Bis[6-(hydroxymethyl)-2pyridyljacetylene (22). To a vigorously stirred, refluxing solution of potassium hydroxide in methanol was added 21 in ca. 50-mg quantities, and the mixture was then refluxed for 30 min. The mixture was concentrated in vacuo to give an off-white solid residue, which was slurried in ice-water, filtered, and recrystallized from ethyl acetate to give 59-72% of pure starting olefin 20, mp 139-140 °C. No acetylenic proudcts were isolated from this reaction sequence.
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