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

HRID 1931782ノート

反応式

HRID 1931782 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8000Boron trifluoride etherate触媒HCID 962Water溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-0d61cdd8d0244f4184f8046bebc76fc4
出典データセット
uspto-grants-2012_05
特許番号
US08188307B2

反応ノート

読み込み中…