Reaktion #427507

Reaktionsgleichung

4-ethynylaniline

triethylamine

acetyl chloride

→

N-(4-ethynylphenyl)acetamide

Lösungsmittel

ethyl acetate

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle