Potassium Fluoride → HCID 59155917, compound

HRID 1662873Notes

Reaction equation

HRID 1662873 reaction equation
I[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([C:28]3[S:29][C:30](I)=[CH:31][CH:32]=3)=[C:10]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])[C:11]=2[P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:39]1[S:43][C:42]([C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)=[C:41]([P:49]([O:54][CH2:55][CH3:56])([O:51][CH2:52][CH3:53])=[O:50])[C:40]=1[P:57]([O:62][CH2:63][CH3:64])([O:59][CH2:60][CH3:61])=[O:58])CCC.[F-].[K+]>C1COCC1.[Cu]Cl>[CH2:15]([O:14][P:12]([C:11]1[C:10]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([C:28]2[S:29][C:30]([C:9]3[S:8][C:7]([C:5]4[S:6][C:2]([C:39]5[S:43][C:42]([C:44]6[S:45][CH:46]=[CH:47][CH:48]=6)=[C:41]([P:49]([O:51][CH2:52][CH3:53])([O:54][CH2:55][CH3:56])=[O:50])[C:40]=5[P:57]([O:59][CH2:60][CH3:61])([O:62][CH2:63][CH3:64])=[O:58])=[CH:3][CH:4]=4)=[C:11]([P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])[C:10]=3[P:20]([O:22][CH2:23][CH3:24])([O:25][CH2:26][CH3:27])=[O:21])=[CH:31][CH:32]=2)[S:8][C:7]=1[C:5]1[S:6][CH:2]=[CH:3][CH:4]=1)([O:17][CH2:18][CH3:19])=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 59155829HCID 59155829, compoundHCID 59155960HCID 59155960, compound

Product 1

HCID 59155917HCID 59155917, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In THF, 0.155 g (0.201 mmols) of the 5,5″-diiodo-3′,4′-bis(diethoxyphosphoryl)-[2,2′;5′,2″]-terthiophene obtained in Example 7(4) and 0.307 g (0.422 mmols) of 5-tributylstannyl-3,4-bis(diethoxyphosphoryl)-[2,2′]-bithiophene obtained in Example 6(5) were dissolved, to which 0.0438 g (0.442 mmols) of commercially available copper(I) chloride was added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 18 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. Subsequently, 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 silica gel column to obtain the specified substance in the form of a yellow oil at a yield of 0.216 g (yield: 77%).

Workup

  1. additionwas added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 18 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 1 hour
  7. customSubsequently, 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 silica gel column
  14. customto obtain the specified substance in the form of a yellow oil at a yield of 0.216 g (yield: 77%)

Sources & evidence

ORD record
ord-f019d0f764ca413fb948f41ae347aeb1
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

Loading…