Reaktion #2018966

Reaktionsgleichung

4-trifluoromethylaniline

methyl 3-oxopentanoate

toluene

→

title compound

Ausbeute 75.8%

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

Ausbeute 75.8%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated in a bath
2. 2
   Temperaturunder reflux
3. 3
   Temperaturcooled
4. 4
   SonstigeThe solvent was evaporated by means of a rotary-evaporator
5. 5
   workup.DISTILLATIONthe residue was distilled under reduced pressure

Vorschrift

In a 2L-flask were placed 4-trifluoromethylaniline (161 g, 1.00 mol), methyl 3-oxopentanoate (143 g, 1.10 mol) and toluene (640 ml). To this solution was added p-toluenesulfonic acid monohydrate (3.2 g, 0.017 mol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 27 kPa, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. After 15 hours, the heating was discontinued, nitrogen leaked in, and the reaction mixture cooled. The solvent was evaporated by means of a rotary-evaporator, and the residue was distilled under reduced pressure to give 207 g of the title compound. The yield was 75.8%.

Quelle