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

HRID 1931782Notes

Reaction equation

HRID 1931782 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 68545758Methyl 3-(4-trifluoromethylphenylamino)-2-pentenoateYield 77.1%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 962WaterSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-0d61cdd8d0244f4184f8046bebc76fc4
Source dataset
uspto-grants-2012_05
Patent number
US08188307B2

Reaction notes

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