Reaktion #2018965

Reaktionsgleichung

4-trifluoromethylaniline

Acetic acid

toluene

acetic acid

Acetic acid

methyl 3-oxopentanoate

→

title compound

Ausbeute 72.8%

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

Ausbeute 72.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated in a bath
2. 2
   Temperaturunder reflux
3. 3
   Temperaturreflux
4. 4
   Temperaturreflux
5. 5
   workup.WAITwas continued for another 2.5 hours
6. 6
   Temperaturcooled
7. 7
   workup.DISTILLATIONAfter distillation of the solvent and acetic acid under reduced pressure
8. 8
   workup.DISTILLATIONthe residue was distilled under reduced pressure

Vorschrift

In a IL-flask were placed 4-trifluoromethylaniline (161 g, 1.00 mol), methyl 3-oxopentanoate (130 g, 1.00 mol) and toluene (160 mL). To this solution was added acetic acid (16 g, 0.27 mol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 19 kPa for 3.5 hours, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. Acetic acid (16 g, 0.27 mol) was then added, and reflux was continued for 4.5 hours. Acetic acid (8 g, 0.13 mol) was then added again, and reflux was continued for another 2.5 hours. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. After distillation of the solvent and acetic acid under reduced pressure, the residue was distilled under reduced pressure to give 199 g of the title compound. The yield was 72.8%. The 1H-NMR spectrum was identical to that of Example 1.

Quelle