تفاعل #351237

معادلة التفاعل

tetrazole

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

triethylamine

acetonitrile

1-bromododecane

→

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

المذيبات

hexane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe suspension was heated
2. 2
   درجة الحرارةto reflux
3. 3
   درجة الحرارةThe solution was refluxed for 16 hours
4. 4
   أخرىthe solvent removed in vacuo
5. 5
   أخرىThe residue was triturated with ethyl acetate
6. 6
   ترشيحfiltered
7. 7
   أخرىconcentration of the filtrate in vacuo leaving a maroon-colored liquid
8. 8
   أخرىThe 2-isomer was obtained
9. 9
   أخرىremoving the impurities

الإجراء التجريبي

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%).

المصدر