Reaction #1725

Reaction equation

sodium hydroxide

4-phenoxyphenylacetonitrile

trimethylsilylazide

dibutyltin oxide

→

5-(4-phenoxyphenylmethyl)-1H-tetrazole

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureto reflux for 19 hours
3. 3
   Washwashed with diethyl ether (3×50 ml)
4. 4
   Washthen washed with 5:1 ethyl acetate/tetrahydrofuran (60 ml) and ethyl acetate (2×50 ml)
5. 5
   DryingThe combined organic layer was dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

To a solution of 4-phenoxyphenylacetonitrile (1.16 g) in anhydrous toluene (30 ml) was added trimethylsilylazide (1.1 ml) and dibutyltin oxide (0.19 g). The mixture was heated to reflux for 19 hours then allowed to cool to room temperature. The reaction mixture was then added to 1M sodium hydroxide (100 ml) and washed with diethyl ether (3×50 ml). The aqueous layer was acidified with concentrated hydrochloric acid (30 ml) then washed with 5:1 ethyl acetate/tetrahydrofuran (60 ml) and ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to give 5-(4-phenoxyphenylmethyl)-1H-tetrazole as a white solid.

Source