Reaktion #2018964

Reaktionsgleichung

4-trifluoromethylaniline

methyl 3-oxopentanoate

toluene

→

title compound

Ausbeute 77.1%

methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate

Ausbeute 77.1%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated under a reduced pressure of 8 kPa
2. 2
   TemperaturThe reaction mixture was heated for 5 hours
3. 3
   Sonstigeproduced
4. 4
   Sonstigewas removed out of the reaction system
5. 5
   TemperaturAfter cooling
6. 6
   Sonstigethe solvent was removed by distillation
7. 7
   Sonstigea rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was then distilled under reduced pressure

Vorschrift

In a 500-ml flask, 4-trifluoromethylaniline (80.6 g, 0.5 mol), methyl 3-oxopentanoate (65.1 g, 0.5 mol) and toluene 400 ml were placed. To this solution was added boron trifluoride etherate (1.42 g, 10 mmol), and the resulting mixture was heated under a reduced pressure of 8 kPa. The reaction mixture was heated for 5 hours under reflux, while water produced was removed out of the reaction system by using a Dean-Stark trap. Then, the heating was discontinued and nitrogen was leaked. After cooling, the solvent was removed by distillation by using a rotary evaporator. The residue was then distilled under reduced pressure to give 105.3 g of the title compound. The yield was 77.1%.

Quelle