Reacción #171523

Ecuación de reacción

3-(13-Bromo-tridecyl)-pyridine

3-picoline

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product

Rendimiento 65.0%

3-methyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromide

Rendimiento 65.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated at 50 C overnight
2. 2
   OtroThe excess picoline was removed in vacuum
3. 3
   Otrothe resulting residue was partitioned between water and ether
4. 4
   LavadoThe aqueous layer was washed extensively with ether until no picoline
5. 5
   workup.WAITleft in the aqueous layer
6. 6
   Extracciónthe aqueous layer was extracted with chloroform
7. 7
   OtroThe chloroform was removed

Procedimiento

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 3-picoline (5 ml), and the mixture was heated at 50 C overnight. The excess picoline was removed in vacuum, and the resulting residue was partitioned between water and ether. The aqueous layer was washed extensively with ether until no picoline left in the aqueous layer, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (65%). 1HNMR (300 MHz, CDCl3, ppm), 9.36 (s, 1H), 9.22 (d, J=5.4, 1H), 8.44 (br, 2H), 8.21 (d, J=7.5, 1H), 7.97 (m, 1H), 7.54 (d, 7.2, 1H), 7.24-7.24 m, 1H), 4.96 (t, J=7.2, 2H), 2.58-2.65 M, 5H), 2.00-2.07 (m, 4H), 1.58-1.60 (m, 2H), 1.20-1.36 (m, 16H); 13CNMR, 148.76, 146.10, 145.58, 144.77, 142.38, 139.83, 137.29, 127.80, 123.98, 62.28, 58.71, 33.31, 32.36, 31.32, 29.80, 29.74, 29.64, 29.38, 29.35, 26.45, 19.15, 18.81.

Fuente