1,2-Dimethoxyethane → 1-Methoxy-4-methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene

HRID 32256ノート

反応式

HRID 32256 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1B(O)O.[CH3:13][C:14]1([CH3:30])[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16](OS(C(F)(F)F)(=O)=O)=[CH:15]1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O.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.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:16]1[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19][C:14]([CH3:30])([CH3:13])[CH:15]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 110873803,3,5,5-Tetramethylcyclohex-1-en-1-yl triflate

生成物 1

HCID 231426761-Methoxy-4-methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene収率 64.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 2-methoxy-5-methylphenylboronic acid (1 g, 6.02 mmol), trifluoromethanesulfonic acid 3,3,5,5-tetramethylcyclohex-1-enyl ester (1.9 g, 6.62 mmol) produced in Example (4a) and 1,2-dimethoxyethane (30 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.30 mmol) and 2N aqueous solution of sodium carbonate (9.0 mL, 18.0 mmol), followed by stirring for 3 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtrated, the resultant filtrate was concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 1.0 g of the title compound as a light yellow oil.

後処理

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationfiltrated
  3. concentrationthe resultant filtrate was concentrated under reduced pressure
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography (ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-77dc1dbde4074c49be33a8a4e9f38c52
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

反応ノート

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