Trifluoroacetic acid → 2-Cyclohexylquinoline

HRID 500456ノート

反応式

HRID 500456 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:11]1(C(O)=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].FC(F)(F)C(O)=O.[OH-].[Na+]>ClC1C=CC=CC=1.[N+]([O-])([O-])=O.[Ag+].O>[CH:11]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

9

反応物 5

HCID 6422Trifluoroacetic acidHCID 7047QuinolineHCID 7413Cyclohexanecarboxylic acidHCID 14798Sodium HydroxideHCID 62648Ammonium Persulfate

生成物 1

HCID 138161892-Cyclohexylquinoline収率 12.6%

試薬・触媒・溶媒 3

HCID 24470Silver Nitrate触媒HCID 962Water溶媒HCID 7964Chlorobenzene溶媒

反応条件

温度
140 °C

実験手順

To a solution of quinoline (11.84 ml, 100 mmol) in chlorobenzene (300 ml) was added sequentially water (300 ml), cyclohexanecarboxylic acid (35.88 g, 280 mmol), silver nitrate (1.36 g, 8.0 mmol), ammonium persulfate (22.82 g, 100 mmol) and trifluoroacetic acid (7.67 g, 100 mmol). The mixture was heated to 140° C. with stirring for 3 h. The mixture was then cooled to room temperature, basified with solid sodium hydroxide and the solvent removed in vacuo. The residue was then subjected to a continuous extraction with isohexane for 18 h, the solvent evaporated under reduced pressure and the residue purified by flash chromatography eluting with 20% (v/v) ethyl acetate in isohexane to afford 2-cyclohexylquinoline as a yellow oil (2.66 g, 12.61 mmol).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe solvent removed in vacuo
  3. extractionThe residue was then subjected to a continuous extraction with isohexane for 18 h
  4. customthe solvent evaporated under reduced pressure
  5. customthe residue purified by flash chromatography
  6. washeluting with 20% (v/v) ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-fe95ad4647da4b808b6880ffccc33cb2
出典データセット
uspto-grants-2010_08
特許番号
US07772227B2

反応ノート

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