Ethanol → 7-(4-Fluorophenyl)-1-tetralone

HRID 1277028ノート

反応式

HRID 1277028 の反応式
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25](O)[CH3:26]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:21]2[CH:22]=[C:23]3[C:18]([CH2:24][CH2:25][CH2:26][C:12]3=[O:15])=[CH:19][CH:20]=2)=[CH:4][CH:5]=1

参加物

7

反応物 4

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 867561584-Fluorophenyl borate

生成物 1

HCID 184723477-(4-Fluorophenyl)-1-tetralone

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

Under argon atmosphere, a mixture of 7-(trifluoromethanesulfoxy)-1-tetralone (17.5 g), 4-fluorophenyl borate (10.0 g), potassium carbonate (16.6 g), toluene (500 ml), ethanol (50 ml) and water (50 ml) was stirred at room temperature for 30 minutes, and to the mixture was added tetrakis(triphenylphosphine)palladium (2.08 g). The mixture was refluxed for 14 hours. The reaction mixture was cooled to room temperature. The organic layer was separated, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene=1/10) to give 7-(4-fluorophenyl)-1-tetralone (13.8 g) as brown oil.

後処理

  1. temperatureThe mixture was refluxed for 14 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate/toluene=1/10)

出典と根拠

ORDレコード
ord-4fd3409745e64b7989d29876974ea564
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

読み込み中…