Cesium fluoride → Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]propanoate

HRID 1690609Notes

Reaction equation

HRID 1690609 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[CH:11][C:12]=1OS(C(F)(F)F)(=O)=O.[CH:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29].[F-].[Cs+]>C(COC)OC.C(O)C>[CH:28]([C:30]1[CH:35]=[CH:34][C:33]([C:12]2[CH:11]=[CH:10][C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:32][CH:31]=1)=[O:29]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 5910734-Formylphenylboronic AcidHCID 86633298Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate

Product 1

HCID 86633297Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]propanoateYield 76.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate (5 g, 12 mmol) was dissolved in dimethoxyethane (70 mL) and ethanol (7 mL). 4-Formylbenzeneboronic acid (2.0 g, 13 mmol) was added and argon was bubbled in the mixture, for 15 minutes. Cesium fluoride (4 g, 26 mmol) and tetrakistriphenylphosphine palladium (0.69 g, 0.6 mmol) were added and the mixture was brought to reflux under an argon atmosphere for 4 hours. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in ethyl acetate/water (100 mL/100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1) to yield 3.42 g (76%) of the desired product as a yellow oil.

Workup

  1. customargon was bubbled in the mixture, for 15 minutes
  2. temperatureto reflux under an argon atmosphere for 4 hours
  3. customsolvents were evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate/water (100 mL/100 mL)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-e93b1ea22b1e40118f2ffbea33b9928b
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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