반응 #51105

반응 방정식

water

4-benzyloxy-2-methoxybenzonitrile

sodium azide

triethylamine hydrochloride

→

5-[4-(benzyloxy)2-methoxyphenyl]-2H-tetrazole

용매

toluene

반응 조건

후처리

1. 1
   온도was heated at 110° for 48 h
2. 2
   온도The brown suspension was cooled
3. 3
   기타The organic layer was separated
4. 4
   추출extracted with water (5 mL)
5. 5
   기타The gum that initially precipitated
6. 6
   workup.STIRRINGupon stirring for 30 min
7. 7
   여과The solid was filtered
8. 8
   세척washed with water
9. 9
   기타dried

실험 절차

A vigorously stirred suspension of 4-benzyloxy-2-methoxybenzonitrile (1-B) (1.20 g, 5.0 mmol), sodium azide (732 mg, 11.3 mmol), and triethylamine hydrochloride (1.54 g, 11.3 mmol) in toluene (6 mL) was heated at 110° for 48 h. The brown suspension was cooled, water (15 mL) was added, and the mixture stirred for 30 min. The organic layer was separated and extracted with water (5 mL). The combined aqueous extracts were acidified to about pH 1 with concentrated HCl. The gum that initially precipitated solidified upon stirring for 30 min. The solid was filtered, washed with water, and dried to give 5-[4-(benzyloxy)2-methoxyphenyl]-2H-tetrazole (1-C). 1H NMR (500 MHz, CDCl3): δ 12.9 (vbs, 1H), 7.37 (d, 1H, J=8.7 Hz), 7.34-7.48 (m, 5H), 6.78 (dd, 1H, J=2.3, 8.7 Hz), 6.70 (d, 1H, J=2.3 Hz), 5.15 (s, 2H), 4.05 (s, 3H) ppm.

출처