Reaktion #51105

Reaktionsgleichung

water

4-benzyloxy-2-methoxybenzonitrile

sodium azide

triethylamine hydrochloride

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated at 110° for 48 h
2. 2
   TemperaturThe brown suspension was cooled
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionextracted with water (5 mL)
5. 5
   SonstigeThe gum that initially precipitated
6. 6
   workup.STIRRINGupon stirring for 30 min
7. 7
   FiltrationThe solid was filtered
8. 8
   Waschenwashed with water
9. 9
   Sonstigedried

Vorschrift

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.

Quelle