Ethanol → 2,2-Dimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuran

HRID 1850372Notes

Reaction equation

HRID 1850372 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.Br[C:22]1[CH:32]=[CH:31][C:25]2[CH2:26][C:27]([CH3:30])([CH3:29])[O:28][C:24]=2[CH:23]=1>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.O.C(COC)OC>[CH3:29][C:27]1([CH3:30])[CH2:26][C:25]2[CH:31]=[CH:32][C:22]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:23][C:24]=2[O:28]1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 111388576-Bromo-2,2-dimethyl-2,3-dihydrobenzofuranHCID 190353504-Methylphenyl dihydrogen borate

Product 1

HCID 667607852,2-Dimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuranYield 56%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

4-methylphenylboric acid (1.35 g, 9.91 mmol), tetrakis(triphenylphosphine)palladium (382 mg, 0.331 mmol), an aqueous solution of 2N sodium carbonate (4.5 mL) and ethanol (83 mL) were sequentially added to a solution of dimethoxyethane (9 mL) containing 6-bromo-2,2-dimethyl-2,3-dihydro-1-benzofuran (1.50 g, 6.61 mmol) synthesized in Reference Example 7, and the mixture was stirred under microwave irradiation at 150° C. for 10 minutes. After cooled to room temperature, water was added to the reaction solution, and extraction was performed using ethyl acetate. The extract was washed with saturated sodium hydrogencarbonate and saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 99:1 to 93/7) to give 880 mg of the title compound (yield: 56%).

Workup

  1. customsynthesized in Reference Example 7
  2. temperatureAfter cooled to room temperature
  3. washThe extract was washed with saturated sodium hydrogencarbonate and saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 99:1 to 93/7)

Sources & evidence

ORD record
ord-adaa6a1ce6eb415a9f093c425b2c951d
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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