Reacción #49890

Ecuación de reacción

product

5-(4-cyanophenyl)-4-pentynyl methanesulfonate

NaN3

→

product

Rendimiento 100.0%

1-(4-cyanophenyl)-5-azido-1-pentyne

Rendimiento 100.0%

Disolventes

water

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat 60° C. for 2 hours
2. 2
   Temperaturacooled to room temperature
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with water (2×)
5. 5
   Secadowith brine and dried (Na2SO4)
6. 6
   OtroEvaporation under reduced pressure

Procedimiento

To a solution of the product of step B (13.40 g, 50.9 mmol) in dimethylformamide (35 mL) was added NaN3 (16.5 g, 255 mmol). The reaction was stirred at room temperature for 18 hours then at 60° C. for 2 hours, cooled to room temperature, diluted with water (400 mL) and extracted with ethyl acetate. The organic layer was washed with water (2×) then with brine and dried (Na2SO4). Evaporation under reduced pressure afforded 10.70 g (100%) of product as a tan oil.

Fuente