Sodium Carbonate → 3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one

HRID 2307100Notes

Reaction equation

HRID 2307100 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1B(O)O.Br[C:25]1[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[CH:26]=1>C(O)C.C(COC)OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1[C:25]1[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[CH:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 109650383-Bromocyclohex-2-enoneHCID 223378172,4-Bis(methoxymethoxy)phenylboronic acid

Product 1

HCID 121351713-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-oneYield 83%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Aqueous sodium carbonate (2 ml of a 6M solution) and 2,4-bis(methoxymethoxy)phenylboronic acid (120 mg) in ethanol (2 ml) were added to a solution of palladium tetrakis(triphenylphosphine) (57 mg) and 3-bromo-2-cyclohexen-1-one (87 mg) in dimethoxyethane (3 ml) and the mixture was heated under reflux. After 6 hr, the mixture was partitioned between water (50 ml) and ethyl acetate (100 ml). The organic layer was dried over magnesium sulfate and evaporated in vacuo to furnish an oil that was purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3, v/v) to furnish the title compound as an oil (120 mg, 83%). δH(CDCl3) 2.10 (2H, quintet), 2.47 (2H, t), 2.74 (2H, m), 3.476 (3H, s), 3.484 (3H, s), 5.185 (2H, s), 5.190 (2H, s), 6.21 (1H, m), 6.71 (1H, dd), 6.85 (1H, d), 7.16 (1H, d).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customthe mixture was partitioned between water (50 ml) and ethyl acetate (100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto furnish an oil that
  7. customwas purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3

Sources & evidence

ORD record
ord-76b944a480174e4f9d59ba7e6c06e334
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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