Toluene → Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoate

HRID 1819730

Reaktionsgleichung

Reaktionsgleichung von HRID 1819730
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.O=[C:13]([CH2:19][CH3:20])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C1(C)C=CC=CC=1>B(F)(F)F.CCOCC.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:13]([CH2:19][CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

Produkt 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoateAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8000Boron trifluoride etherateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  1. temperaturethe resulting mixture was heated under a reduced pressure of 8 kPa
  2. temperatureThe reaction mixture was heated for 5 hours
  3. customproduced
  4. customwas removed out of the reaction system
  5. temperatureAfter cooling
  6. customthe solvent was removed by distillation
  7. customa rotary evaporator
  8. distillationThe residue was then distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bf4b865e14794cddbdabd286f9589ba3
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601842B2

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