Potassium Fluoride → 3,4',4'',4'''-Tetrakis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''']-quaterthiophene

HRID 1662888Notes

Reaction equation

HRID 1662888 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:10]=[C:11]([C:14]2[S:15][C:16](I)=[CH:17][C:18]=2[P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[S:12][CH:13]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:33]1[S:37][C:36]([C:38]2[S:39][CH:40]=[CH:41][C:42]=2[P:43]([O:48][CH2:49][CH3:50])([O:45][CH2:46][CH3:47])=[O:44])=[CH:35][C:34]=1[P:51]([O:56][CH2:57][CH3:58])([O:53][CH2:54][CH3:55])=[O:52])CCC.[Cu]C#N.[F-].[K+]>C1(C)C=CC=CC=1>[CH2:22]([O:21][P:19]([C:18]1[CH:17]=[CH:16][S:15][C:14]=1[C:11]1[S:12][C:13]([C:40]2[S:39][C:38]([C:36]3[S:37][CH:33]=[C:34]([P:51]([O:56][CH2:57][CH3:58])([O:53][CH2:54][CH3:55])=[O:52])[CH:35]=3)=[C:42]([P:43]([O:45][CH2:46][CH3:47])([O:48][CH2:49][CH3:50])=[O:44])[CH:41]=2)=[C:9]([P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH:10]=1)([O:24][CH2:25][CH3:26])=[O:20])[CH3:23]

Participants

6

Reactant 4

HCID 522689Potassium FluorideHCID 591558305-(Tributylstannyl)-4,3'-bis(diethoxyphosphoryl)-[2,2']-bithiopheneHCID 591558664,3'-Bis(diethoxyphosphoryl)-5'-iodo-[2,2']-bithiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 591559263,4',4'',4'''-Tetrakis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''']-quaterthiopheneYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 0.0564 g (0.1 mmol) of 4,3′-bis(diethoxyphosphoryl)-5′-iodo-[2,2′]-bithiophene and 0.0092 g (0.008 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 2 ml of toluene, to which 0.0709 g (0.1 mmol) of 5-(tributylstannyl)-4,3′-bis(diethoxyphosphoryl)-[2,2′]-bithiophene and 0.0018 g (0.02 mmols) of commercially available copper(I) cyanide were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 2.5 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution added, followed by stirring for 1 hour. 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 PTLC plate (developed with ethyl acetate and ethyl acetate:hexane=15:1) to obtain the specified substance in the form of an orange oil at a yield of 0.0717 g (yield: 82%).

Workup

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 2.5 hours
  4. customAfter the reaction
  5. additionadded
  6. stirringby stirring for 1 hour
  7. customThe resulting 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 and ethyl acetate:hexane=15:1)
  14. customto obtain the specified substance in the form of an orange oil at a yield of 0.0717 g (yield: 82%)

Sources & evidence

ORD record
ord-6960887afea04cb7b87d7c481db915d9
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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