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ChemicalBook CAS DataBase List 4,4'-Vinylenedipyridine
13362-78-2

4,4'-Vinylenedipyridine synthesis

5synthesis methods
-

Yield:13362-78-2 49%

Reaction Conditions:

with acetic acid;lithium diisopropyl amide in tetrahydrofuran at -70; for 24 h;Darkness;Reflux;Knoevenagel Condensation;

Steps:

Ligand pypy
400μL (4.12mmol) of 4-picoline reacted with 3.0mL (4.32mmol) of LDA in THF (5mL) at -70°C. In the absence of light, 465mL (4.12mmol) of 4-piridincarboxyaldehyde was dropwise added with continuous stirring. After 24h of reflux in the presence of 10mL of acetic acid, the reaction mixture led to a yellow solution, from which a pale-yellow solid was separated by rotatory evaporation. The solid was purified employing column chromatography in analogous conditions to the ones previously mentioned (368mg, 49%). 1H RMN (400MHz, CDCl3, δ): 8.62 (d, J=4Hz, 4H, Ar-H), 7.61 (d, J=4Hz, 4H, Ar-H), 7.55 (s, 2H, -CH=CH-).

References:

Luzardo, Florencia;álvarez, Natalia;Kremer, Carlos;de Camargo, Andrea S.S.;Gancheff, Jorge S. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2017,vol. 183,p. 45 - 52]

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