Reacción #427507

Ecuación de reacción

4-ethynylaniline

triethylamine

acetyl chloride

→

N-(4-ethynylphenyl)acetamide

Disolventes

ethyl acetate

water

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter warmed to ambient temperature
2. 2
   OtroThe two phases were separated
3. 3
   Extracciónthe aqueous layer was extracted twice with ethyl acetate
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried over anhydrous MgSO4
6. 6
   Concentraciónconcentrated en vacuo
7. 7
   OtroThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Procedimiento

To a solution of 4-ethynylaniline (commercially available) (1.0 eq.), and triethylamine (1.0 eq.) in methylene chloride (0.04 M), acetyl chloride (1.5 eq.) was added slowly. Then the reaction mixture was stirred at 0° C. for 1 hour. After warmed to ambient temperature, the reaction mixture was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give N-(4-ethynylphenyl)acetamide as a white solid.

Fuente