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

HRID 1582797ノート

反応式

HRID 1582797 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e0224a13d0ac415ba89b98ed2d06a19e
出典データセット
uspto-grants-2004_05
特許番号
US06737417B2

反応ノート

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