Water → 6-Methoxy-2-(4-methoxyphenyl)-1-(2-propenyl)naphthalene

HRID 460448노트

반응식

HRID 460448 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].FC(F)(F)S(O[C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:37][CH3:38])[CH:33]=2)[C:28]=1[CH2:39][CH:40]=[CH2:41])(=O)=O.O>O1CCOCC1.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>[CH3:38][O:37][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[C:28]([CH2:39][CH:40]=[CH2:41])=[C:27]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH:36]=[CH:35]2

참가 물질

7

반응물 4

HCID 962WaterHCID 201262(4-Methoxyphenyl)boronic acidHCID 207268476-Methoxy-1-(2-propenyl)-2-naphthyl trifluoromethanesulfonateHCID 22031701Potassium phosphate, tribasic, monohydrate

생성물 1

HCID 227180106-Methoxy-2-(4-methoxyphenyl)-1-(2-propenyl)naphthalene수율 75%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

4-Methoxyphenylboronic acid (10.15 g, 66.8 mmol), tripotassium phosphate hydrate (77.6 g, 278.3 mmol) and tetrakis(triphenylphosphine)palladium(0)(1.93 g, 1.67 mmol, 3 mol %) were added to a solution of 6-methoxy-1-(2-propenyl)-2-naphthyl trifluoromethanesulfonate (19.3 g, 55.66 mmol) in dioxane (300 ml), followed by heating under reflux for 8 hours under argon atmosphere. Water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9), followed by recrystallization from hexane, to give 6-methoxy-2-(4-methoxyphenyl)-1-(2-propenyl)naphthalene (12.65 g, Yield 75%).

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 8 hours under argon atmosphere
  3. extractionwas then extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9)
  8. customfollowed by recrystallization from hexane

출처 및 근거

ORD 기록
ord-0f9820b897124778ac8efa1f1005aa6f
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196081B2

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