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

HRID 394852Notes

Reaction equation

HRID 394852 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>[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

5

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 61.3%

Reagents, catalysts & solvents 1

HCID 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, 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(.)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). MS (EI): m/z 282 (M+).

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-15578402dcea403a940d993ed4efc6d3
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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