4,4'-Vinylenedipyridine synthesis
- Product Name:4,4'-Vinylenedipyridine
- CAS Number:13362-78-2
- Molecular formula:C12H10N2
- Molecular Weight:182.22
108-89-4
872-85-5
13362-78-2
The general procedure for the synthesis of 1,2-bis(4-pyridyl)ethene from 4-methylpyridine and 4-pyridinecarboxaldehyde was as follows: 400 μL (4.12 mmol) of 4-methylpyridine was reacted with 3.0 mL (4.32 mmol) of a solution of LDA in THF (5 mL) at -70 °C. Under light-avoiding conditions, 465 μL (4.12 mmol) of 4-pyridinecarboxaldehyde was added by continuous stirring and slow dropwise addition. Subsequently, the reaction mixture was refluxed in the presence of 10 mL of acetic acid for 24 h. The reaction mixture was observed to transform into a yellow solution. The light yellow solid product was isolated from this solution by rotary evaporation. Purification of the solid product using column chromatography under similar conditions afforded 368 mg (49% yield) of the target compound.1H NMR (400 MHz, CDCl3, δ): 8.62 (d, J = 4Hz, 4H, Ar-H), 7.61 (d, J = 4Hz, 4H, Ar-H), 7.55 (s, 2H, -CH=CH-).
108-89-4
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$15.00/25mL
872-85-5
500 suppliers
$10.00/1g
13362-78-2
187 suppliers
$9.00/250mg
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]
108-89-4
345 suppliers
$15.00/25mL
13362-78-2
187 suppliers
$9.00/250mg
4916-57-8
129 suppliers
$30.00/250mg
13362-78-2
187 suppliers
$9.00/250mg
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13362-78-2
187 suppliers
$9.00/250mg