Abstract 2‐Methyl‐4‐(4‐pyridyl)‐3‐butyn‐2‐ol (2) was prepared in 70% yield by the reaction of 4‐bromopyridine with 2‐methyl‐3‐butyn‐2‐ol in diethylamine in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide. Removal of the protective group in 2 by refluxing with sodium hydroxide in toluene yields (90%) 4‐ethynylpyridine (3). Oxidative coupling of 3 in pyridine by dioxygen in the presence of copper(I) chloride produces a 92% yield of 1,4‐bis(4‐pyridyl)butadiyne.
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Ciana et al. (1984) studied this question.
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