反応 #51105

反応方程式

water

4-benzyloxy-2-methoxybenzonitrile

sodium azide

triethylamine hydrochloride

→

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

溶媒

toluene

反応条件

後処理

1. 1
   温度was heated at 110° for 48 h
2. 2
   温度The brown suspension was cooled
3. 3
   その他The organic layer was separated
4. 4
   抽出extracted with water (5 mL)
5. 5
   その他The gum that initially precipitated
6. 6
   workup.STIRRINGupon stirring for 30 min
7. 7
   ろ過The solid was filtered
8. 8
   洗浄washed with water
9. 9
   その他dried

実験手順

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.

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