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

HRID 2086626Notes

Reaction equation

HRID 2086626 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-630304d2a1714ae5afb74432fac58629
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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