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

HRID 2218900Notes

Reaction equation

HRID 2218900 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-86f35078472841049f3d476a88959631
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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