反応 #46735

反応方程式

2-hydroxyoctyloxy-benzonitrile

sodium azide

triethylamine hydrochloride

NaOH

→

5-Octyloxy-2-(1H-tetrazol-5-yl)-phenol

溶媒

H2O

toluene

EtOAc

反応条件

後処理

1. 1
   その他The precipitate formed
2. 2
   その他The organic phase was isolated
3. 3
   抽出extracted with 4 M NaOH (aq)
4. 4
   その他the precipitate formed
5. 5
   その他isolated by filtration
6. 6
   その他to yield 240 mg (82%) as a purple solid
7. 7
   その他after drying

実験手順

A slurry of 2-hydroxyoctyloxy-benzonitrile (247 mg; 1 mmol), sodium azide (195 mg; 3 mmol), triethylamine hydrochloride (411 mg; 3 mmol) was refluxed in toluene (5 mL) under N2 for 4 hours after which time the reaction mixture was poured onto H2O 0 (10 mL). The precipitate formed was dissolved by addition of 10 M NaOH (aq) and EtOAc. The organic phase was isolated and extracted with 4 M NaOH (aq). The combined aqueous phases was acidified using 12 M HCl (aq) and the precipitate formed isolated by filtration to yield 240 mg (82%) as a purple solid after drying. Mp. 142-146° C. MS (Direct; Cl): 291 (MH+).

出典