Potassium Fluoride → HCID 86638419, compound

HRID 1662892Notes

Reaction equation

HRID 1662892 reaction equation
[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[C:16](I)[S:15][CH:14]=1)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:19]([O:23][P:24]([C:31]1[CH:35]=[C:34]([Sn](CCCC)(CCCC)CCCC)[S:33][CH:32]=1)([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH2:20][CH2:21][CH3:22].[Cu]C#N.[F-].[K+]>C1(C)C=CC=CC=1>[CH2:1]([O:5][P:6]([C:13]1[CH:17]=[C:16]([C:34]2[S:33][CH:32]=[C:31]([P:24]([O:23][CH2:19][CH2:20][CH2:21][CH3:22])([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH:35]=2)[S:15][CH:14]=1)([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 522689Potassium FluorideHCID 59155811HCID 59155811, compoundHCID 86638420HCID 86638420, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86638419HCID 86638419, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 0.0804 g (0.2 mmols) of 3-(dibutoxyphosphoryl)-5-iodothiophene and 0.0092 g (0.008 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 2 ml of toluene, to which 0.1131 g (0.2 mmols) of 3-(dibutoxyphosphoryl)-5-(tributylstannyl)-thiophene and 0.0036 g (0.04 mmols) of commercially available copper(I) cyanide were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 2 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution was added, followed by stirring for 1 hour. Thereafter, the solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=1:2 and ethyl acetate:hexane=1:1) to obtain the specified substance in the form of a white solid at a yield of 0.0881 g (yield: 80%).

Workup

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 1 hour
  7. customThereafter, the solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe organic phase was washed with a saturated saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed
  12. distillationby distilling off under reduced pressure
  13. customthe resulting crude product was purified with a PTLC plate (developed with ethyl acetate:hexane=1:2 and ethyl acetate:hexane=1:1)
  14. customto obtain the specified substance in the form of a white solid at a yield of 0.0881 g (yield: 80%)

Sources & evidence

ORD record
ord-cb7e75adfa40435781dd74ef126edd76
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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