Toluene → 7-Phenyl-1-tetralone

HRID 1489552

反応式

HRID 1489552 の反応式
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH2:13][C:14]2=[O:17])=[CH:9][CH:8]=1)(=O)=O.[C:20]1(OB(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O>[C:20]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 110008715,6,7,8-Tetrahydro-8-oxo-2-naphthalenyl 1,1,1-trifluoromethanesulfonate

生成物 1

HCID 37782357-Phenyl-1-tetralone収率 82.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

While stirring a mixture comprising 15.32 g (52.06 mmol) of 7-trifluoromethanesulfonyloxy-3,4-dihydro-1(2H)-naphthalenone obtained in the Synthesis Example A-1, 12.7 g (104.12 mmol) of phenylboric acid, 10.8 g (78.09 mmol) of potassium carbonate and 450 ml of toluene at room temperature, nitrogen gas was bubbled thereinto for 30 minutes. Next, 1.81 g (1.57 mmol) of tetrakistriphenylphosphine palladium was added thereto. The mixture was slowly heated to thereby maintain the bulk temperature at about 90° C. After stirring at this temperature for 90 minutes, the reaction mixture was cooled and water was added thereto. The insoluble matters were filtered through celite and thoroughly washed with ethyl acetate. The organic phase was collected, washed successively with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N hydrochloric acid, water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. After successively eluting with hexane:ethyl acetate in a ratio ranging from 20:1 (v/v) to 12:1 (v/v), 9.53 g of the title compound was obtained as white crystals. Yield 82%.

後処理

  1. customnitrogen gas was bubbled
  2. temperatureThe mixture was slowly heated
  3. temperaturethe reaction mixture was cooled
  4. filtrationThe insoluble matters were filtered through celite and
  5. washthoroughly washed with ethyl acetate
  6. customThe organic phase was collected
  7. washwashed successively with a saturated aqueous solution of sodium hydrogencarbonate, water, 1N hydrochloric acid, water
  8. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure
  10. washAfter successively eluting with hexane

出典と根拠

ORDレコード
ord-dc828b2e6d30423fa28d3dafcaa74500
出典データセット
uspto-grants-1997_10
特許番号
US05679671

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