Toluene → 7-Phenyl-1-tetralone

HRID 1489552

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HRID 1489552 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 37782357-Phenyl-1-tetralone수율 82.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-dc828b2e6d30423fa28d3dafcaa74500
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679671

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