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1-(p-Fluorophenyl)-2-(2′-pyridyl)ethanol and 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene obtained from the condensation reaction of 2-picoline and p-fluorophenylaldehyde under catalyst- and solvent-free conditions

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The novel intermediate 1-(p-fluorophenyl)-2-(2′-pyridyl)ethanol or 2-[2′-(1-hydroxy-1-(p-fluorophenyl)ethyl]pyridine and the corresponding novel dehydration compound 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene or 2-[p-fluorophenylvinyl]pyridine were obtained from the condensation reaction of p-fluorophenylaldehyde and 2-picoline under catalyst- and solvent-free conditions. The intermediate 1-(p-fluorophenyl)-2-(2-pyridyl)ethanol was obtained at 42 h reaction time and temperature of 120°C, respectively. 1H-NMR, IR spectroscopic data of the 1-(p-fluorophenyl)-2-(2-pyridyl)ethanol clearly showed the presence of the –CH2–CHOH– group. The compound was obtained as a white powder with m.p. 121–122°C and a yield of 8%. For 1-(p-fluorophenyl)-2-(2-pyridyl)ethene, the reaction conditions were similar, but the reaction temperature was increased to yield the double bond in the 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene. At the reaction temperature of 140°C, the compound was a slightly brown powder with a m.p. of 78°C and yield of 18%. 1H-NMR, IR spectroscopic data for the 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene showed the presence of a double bond in trans configuration (–CH=CH–), characteristic of a styrylpyridine.

Affiliations: 1: Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 194, 22 Sur y San. Claudio, C.P. 72570, Puebla, Puebla, México; 2: División de Estudios de Posgrado, Facultad de Ciencias Químicas, U.A.N.L., Guerrero y Progreso S/N, Col. Treviño, C.P. 64570 Monterrey, N.L., México

10.1163/156856707781749946
/content/journals/10.1163/156856707781749946
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/content/journals/10.1163/156856707781749946
2007-07-01
2016-12-07

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