Water → 3-Acetyl-2,4-dimethyl-5-(4-pyridyl)furan

HRID 2121704Notes

Reaction equation

HRID 2121704 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7](Br)[O:6][C:5]=1[CH3:11])(=[O:3])[CH3:2].O.C([O-])(O)=O.[Na+].[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)[O:6][C:5]=1[CH3:11])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acid2×HCID 15384498HCID 15384498, compound

Product 1

HCID 98372883-Acetyl-2,4-dimethyl-5-(4-pyridyl)furanYield 31%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 3-acetyl-5-bromo-2,4-dimethylfuran (0.8 g, 3.69 mmol) in dimethoxyethane (DME; 11 mL) was added water (4 mL), NaHCO3 (0.93 g, 11 mmol), 4-pyridineboronic acid [prepared according to the method of Fischer F. C. et al., J. Red. Trav. Chim. Pays-Bays, 1965, 84, 439.] (0.5 g, 4.06 mmol) and bis(triphenylphosphine)palladium(II)chloride (0.26 g, 0.37 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 8 hours, and cooled down to room temperature. 4-Pyridineboronic acid (0.5 g, 4.07 mmol) and bis(triphenylphosphine)palladium(II)chloride (1.48 g, 2.11 mmol) were additionally added to the reaction mixture, and heated at reflux temperature for 3.5 hours. After cooling, the reaction mixture was filtered through celite pad. The filtrate was diluted with ethyl acetate (50 mL), and the whole was washed with water (30 mL). The aqueous layer was extracted with ethyl acetate (30 mL), and the combined organic layers were washed with brine (50 mL), dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with ethyl acetate-hexane (5:1) to give the title compound (0.25 g, 31% yield).

Workup

  1. customprepared
  2. customat room temperature
  3. temperatureThe mixture was heated
  4. temperatureat reflux temperature for 8 hours
  5. temperatureheated
  6. temperatureat reflux temperature for 3.5 hours
  7. temperatureAfter cooling
  8. filtrationthe reaction mixture was filtered through celite pad
  9. additionThe filtrate was diluted with ethyl acetate (50 mL)
  10. washthe whole was washed with water (30 mL)
  11. extractionThe aqueous layer was extracted with ethyl acetate (30 mL)
  12. washthe combined organic layers were washed with brine (50 mL)
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated in vacuo
  15. customThe resulting residue was purified by flash chromatography
  16. washeluting with ethyl acetate-hexane (5:1)

Sources & evidence

ORD record
ord-f1ae0308804a405293a320628be0ede9
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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