Reacción #351237

Ecuación de reacción

tetrazole

5-(2-Pyridylmethyl)-1H-tetrazole

triethylamine

acetonitrile

1-bromododecane

→

4-(2-pyridylmethyl)-2-dodecyl-2H-tetrazole

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe suspension was heated
2. 2
   Temperaturato reflux
3. 3
   TemperaturaThe solution was refluxed for 16 hours
4. 4
   Otrothe solvent removed in vacuo
5. 5
   OtroThe residue was triturated with ethyl acetate
6. 6
   Filtraciónfiltered
7. 7
   Otroconcentration of the filtrate in vacuo leaving a maroon-colored liquid
8. 8
   OtroThe 2-isomer was obtained
9. 9
   Otroremoving the impurities

Procedimiento

The tetrazole (a) (3.0 g; 0.015 moles) was taken up in acetonitrile (50 mL) containing two equivalents of triethylamine (3.0 g; 0.030 moles). The suspension was heated to reflux and then treated with 1-bromododecane (3.7 g; 0.015 moles) dropwise for several minutes. The solution was refluxed for 16 hours, cooled to room temperature, and the solvent removed in vacuo. The residue was triturated with ethyl acetate, filtered, and concentration of the filtrate in vacuo leaving a maroon-colored liquid. The 2-isomer was obtained by dissolving the crude product in 50% hexane/50% ethyl acetate and removing the impurities, including the 1-regioisomer, by silica gel chromatography. Yield: 2.0 g (41%).

Fuente