Reacción #6819

Ecuación de reacción

t-butyl alcohol

5-phenylpent-4-ynoic acid

diphenylphosphoryl azide

triethylamine

→

(4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was refluxed for 16 h
2. 2
   Otrothe volatile materials were removed via a rotary evaporator
3. 3
   OtroThe residue was purified by column chromatography on silica (2–6% ethyl acetate in hexanes)

Procedimiento

A solution of 5-phenylpent-4-ynoic acid (0.49 g), diphenylphosphoryl azide (0.66 mL) and triethylamine (0.43 mL) was refluxed in 15 mL toluene for 3 h. The reaction was cooled to rt and t-butyl alcohol was added. The reaction was refluxed for 16 h, then the volatile materials were removed via a rotary evaporator. The residue was purified by column chromatography on silica (2–6% ethyl acetate in hexanes) to give (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (0.3 g).

Fuente