Lithium Chloride → HCID 22316627, compound

HRID 497210Notes

Reaction equation

HRID 497210 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][C:5]=1[CH3:18])(=[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])=[C:5]([CH3:18])[CH:6]=1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 114829354-Acetyl-3-methylphenyl trifluoromethanesulfonate

Product 1

HCID 22316627HCID 22316627, compoundYield 92%

Reagents, catalysts & solvents 3

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

Procedure

To a stirred solution of trifluoromethanesulfonic acid 4-acetyl-3-methylphenyl ester (1.76 g, 6.25 mmol) in dioxane (60 ml) was added 2-(tributylstannyl)furan (2.68 g, 7.5 mmol), lithium chloride (0.66 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.722 g, 0.62 mmol) under nitrogen. The mixture was heated at reflux 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 potassium fluoride 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 (1.15 g, 92%).

Workup

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

Sources & evidence

ORD record
ord-44c8e0d679ea48bfa8e159f0960784ba
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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