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

HRID 32251노트

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HRID 32251 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f1e3eb10a5b247ef95e4208d5352e5da
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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