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

HRID 32256

Reaktionsgleichung

Reaktionsgleichung von HRID 32256
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 231426761-Methoxy-4-methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzeneAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-77dc1dbde4074c49be33a8a4e9f38c52
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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