Lithium Chloride → HCID 22316761, compound

HRID 396778Notes

Reaction equation

HRID 396778 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][O:11][CH:12]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.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:11]1[CH:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:18](=[O:20])[CH3:19])=[CH:3][CH:4]=2)[N:9]=[CH:10]1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 223165954-(4-Bromophenyl)-1,3-oxazole

Product 1

HCID 22316761HCID 22316761, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-(4-bromophenyl)-1,3-oxazole (469 mg, 2.09 mmol) in dioxane (20 ml) was added tributyl(1-ethoxyvinyl)tin (906 mg, 2.51 mmol), tetrakis(triphenylphosphine)palladium (240 mg, 0.207 mmol), lithium chloride (221 mg, 5.23 mmol), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, and diluted with ethyl acetate. The whole was washed with saturated potassium fluoride aqueous solution, and the precipitate was removed by filteration through celite. The resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. To the residue was added THF (10 ml), 2N HCl aqueous solution (10 ml), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, made neutral by addition of NaHCO3, and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (256 mg, 65% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. washThe whole was washed with saturated potassium fluoride aqueous solution
  4. customthe precipitate was removed by filteration through celite
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. additionTo the residue was added THF (10 ml), 2N HCl aqueous solution (10 ml)
  10. temperaturethe mixture was heated
  11. temperatureat reflux temperature for 8 hours
  12. temperatureThe reaction mixture was cooled down to room temperature
  13. additionmade neutral by addition of NaHCO3
  14. extractionextracted with ethyl acetate
  15. washThe organic layer was washed with brine
  16. dry with materialdried over MgSO4
  17. concentrationconcentrated in vacuo
  18. customThe residue was purified by flash chromatography
  19. washeluting with ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-f6609bb4e0674ca2949f920a4c3b834f
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

Loading…