Sodium Bicarbonate → 4,4,4-Trifluoro-1-[4-(2-furyl)phenyl]butane-1,3-dione

HRID 2086653Notes

Reaction equation

HRID 2086653 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3](=[O:14])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)=[O:6].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.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>[F:1][C:2]([F:16])([F:15])[C:3](=[O:14])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:18]2[O:17][CH:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734357Furan-2-boronic acidHCID 27714771-(4-Bromophenyl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 121141604,4,4-Trifluoro-1-[4-(2-furyl)phenyl]butane-1,3-dioneYield 61.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 4,4,4-trifluoro-1-(4-bromophenyl)butane-1,3-dione (1 g, 3.39 mmol, prepared according to the method of J.Med.Chem., 1997, 40, 1347) in DME (40 mL) was added furan-2-boronic acid (0.455 g, 4.07 mmol), bis(triphenylphosphine)palladium(II)chloride (0.271 g, 0.386 mmol) and saturated NaHCO3 solution (12 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 5 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (30 mL×3). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3/1) to give the subtitle compound (0.586 g, 61.2% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 5 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additionthe filtrate was poured into water
  5. extractionthe whole was extracted with ethyl acetate (30 mL×3)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-51681a23a0db48928ffbfe830b6a593e
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

Loading…