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

HRID 2218894Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a16626564ad44c4dbb1cd6f54734a224
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410971B2

Reaction notes

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