Toluene → 7-Phenyl-1-tetralone

HRID 565833ノート

反応式

HRID 565833 の反応式
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]1(OB([O-])[O-])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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.C(O)C>[C:12]1([C:8]2[CH:9]=[C:10]3[C:5]([CH2:4][CH2:3][CH2:2][C:1]3=[O:11])=[CH:6][CH:7]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 107241-TetraloneHCID 11430Potassium CarbonateHCID 19793864Phenylborate

生成物 1

HCID 37782357-Phenyl-1-tetralone収率 78.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 7- (trifluoromethanesulfoxy) -1-tetralone (23.3 g), phenylborate (11.8 g), potassiumcarbonate (21.9 g), toluene (500 ml), ethanol (50 ml) and water (50 ml) was stirred for 30 minutes at room temperature under argon atmosphere, and to the mixture was added tetrakis(triphenylphosphine)palladium (3.66 g). The mixture was refluxed for 20 hours and then cooled to room temperature. The organic layer was separated, washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene/hexane=1/5/5) to give 7-phenyl-1-tetralone (15.1 g) as pale brown oil.

後処理

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified with column chromatography (ethyl acetate/toluene/hexane=1/5/5)

出典と根拠

ORDレコード
ord-3d159f5def2a4171894e1b3528ca33ed
出典データセット
uspto-grants-2001_01
特許番号
US06172061B2

反応ノート

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