Potassium Fluoride → HCID 86638406, compound

HRID 1662865Notes

Reaction equation

HRID 1662865 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][C:10]=1I)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Cu]C#N.C([Sn](CCCC)(CCCC)[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)CCC.[F-].[K+]>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:3][P:4]([C:9]1[C:13]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][S:11][C:10]=1[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 86638408HCID 86638408, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86638406HCID 86638406, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

3,4-bis(diethoxyphosphoryl)-2-iodothiophene, different types of palladium catalysts (0.05 equivalents, commercially available products) indicated in the following Table 5 and commercially available copper(I) cyanide (0.20 equivalents) were dissolved in toluene, to which 2-tributylstannylthiophene (1.2 equivalents) was added at room temperature. Thereafter, the reaction mixture was heated to 70° C. and stirred for 8.5 to 10 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 2 hours. The resulting 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 silica gel column (ethyl acetate:methanol=15:1) to obtain the specified substances.

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. additionwas added
  4. stirringby stirring for 2 hours
  5. customThe resulting solid was removed by celite filtration
  6. extractionthe filtrate was extracted with ethyl acetate
  7. washThe organic phase was washed with a saturated saline solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed
  10. distillationby distilling off under reduced pressure
  11. customthe resulting crude product was purified with a silica gel column (ethyl acetate:methanol=15:1)
  12. customto obtain the specified substances

Sources & evidence

ORD record
ord-893e356f0929465999506dc54dd742e0
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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