Lithium Chloride → 1-[4-(2-Furyl)-3-methylphenyl]ethanone

HRID 396738Notes

Reaction equation

HRID 396738 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([CH3:18])[CH:5]=1)(=[O:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)CCC.[Cl-].[Li+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=1[CH3:18]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 213024274-Acetyl-2-methylphenyl trifluoromethanesulfonate

Product 1

HCID 223166331-[4-(2-Furyl)-3-methylphenyl]ethanoneYield 100.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of trifluoromethanesulfonic acid 4-acetyl-2methylphenyl ester (1.19 g, 4.2 mmol) in 1,4-dioxane (40 mL) was added 2-(tributylstannyl)furan (1.81 g, 5.05 mmol), lithium chloride (0.45 g, 10.5 mmol) and tetrakis(triphenylphosphine)palladium (0.49 g, 0.42 mmol) under nitrogen. The mixture was heated at reflex temperature for 2 hours, and cooled down to room temperature. The reaction mixture was diluted with water and the whole was extracted with diethylether. The organic layer was washed with saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1/10) to give title compound (0.845 g, quant).

Workup

  1. temperatureThe mixture was heated at reflex temperature for 2 hours
  2. extractionthe whole was extracted with diethylether
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-2e1f64e3f2a2459c8ea3d1f3111687b9
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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