1,2-Dimethoxyethane → 2-(3,3,5,5-Tetramethylcyclohex-1-enyl)phenol

HRID 32251ノート

反応式

HRID 32251 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])O1.[CH3:17][C:18]1([CH3:34])[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20](OS(C(F)(F)F)(=O)=O)=[CH:19]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>[CH3:17][C:18]1([CH3:34])[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:19]1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 110873803,3,5,5-Tetramethylcyclohex-1-en-1-yl triflate

生成物 1

HCID 231425262-(3,3,5,5-Tetramethylcyclohex-1-enyl)phenol収率 101%

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-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenol(3.5 g, 15.9 mmol), trifluoromethanesulfonic acid 3,3,5,5-tetramethylcyclohex-1-enyl ester (5 g, 17.4 mmol) produced in Example (4a) and 1,2-dimethoxyethane (20 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.79 mmol) and 2N aqueous solution of sodium carbonate (23.9 mL, 47.7 mmol), followed by stirring for 1 hour 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 then the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 3.7 g of the title compound as a yellow oil.

後処理

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-f1e3eb10a5b247ef95e4208d5352e5da
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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