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5-ethynylpyridine-2-carbonitrile synthesis

3synthesis methods
2-Pyridinecarbonitrile, 5-(3-hydroxy-3-methyl-1-butyn-1-yl)-

1531598-55-6
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5-ethynylpyridine-2-carbonitrile

1211584-19-8
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Yield:1211584-19-8 77%

Reaction Conditions:

with sodium hydride in toluene;mineral oil;Dean-Stark;Reflux;

Steps:

General procedure for acetylenes 56a-d

General procedure: A mixture of the protected acetylene 55 (20-50mmol) and NaH (60% dispersion in mineral oil, 0.15equiv) in toluene in a round bottom flask fitted with a Dean-Stark trapped capped by a reflux condenser was refluxed for 0.75-1.5h. The cooled reaction mixture was filtered through silica gel. The filtrate was evaporated and chromatographed on silica gel eluting with hexanes/EtOAc. The product was recrystallized from hexanes.

References:

Patrick, Donald A.;Bakunov, Stanislav A.;Bakunova, Svetlana M.;Wenzler, Tanja;Brun, Reto;Tidwell, Richard R. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 1,p. 559 - 576]