Trimethylsilyl iodide → 3',4'-Diphosphono-[2,2';5',2'']-terthiophene

HRID 1662877Notes

Reaction equation

HRID 1662877 reaction equation
C([O:3][P:4]([C:9]1[C:13]([P:14]([O:19]CC)([O:16]CC)=[O:15])=[C:12]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[S:11][C:10]=1[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)([O:6]CC)=[O:5])C.I[Si](C)(C)C>C(#N)C>[P:4]([C:9]1[C:13]([P:14]([OH:16])([OH:19])=[O:15])=[C:12]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[S:11][C:10]=1[C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 591559493',4'-Bis(diethoxyphosphoryl)-[2,2':5',2'']-terthiophene

Product 1

HCID 591558713',4'-Diphosphono-[2,2';5',2'']-terthiopheneYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile, 0.2478 g (0.476 mmols) of 3′,4′-bis(diethoxyphosphoryl)-[2,2′;5′,2″]-terthiophene was dissolved, to which 0.4762 g (2.380 mmols) of commercially available iodotrimethylsilane was added at room temperature. Thereafter, the mixture was stirred at room temperature for 12 hours. After the reaction, the solvent was removed by distilling off under reduced pressure, followed by addition of methanol and stirring at room temperature for further 12 hours. The methanol was removed by distilling off under reduced pressure, followed by addition of distilled water under stirring and separation of an aqueous phase. The thus separated aqueous phase was washed several times with chloroform and the aqueous phase was concentrated and evaporated to dryness to obtain the specified substance in the form of yellow crystals at a yield of 0.1742 g (yield: 90%).

Workup

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. customthe solvent was removed
  4. distillationby distilling off under reduced pressure
  5. additionfollowed by addition of methanol
  6. stirringstirring at room temperature for further 12 hours
  7. customThe methanol was removed
  8. distillationby distilling off under reduced pressure
  9. additionfollowed by addition of distilled water
  10. stirringunder stirring
  11. customseparation of an aqueous phase
  12. washThe thus separated aqueous phase was washed several times with chloroform
  13. concentrationthe aqueous phase was concentrated
  14. customevaporated to dryness
  15. customto obtain the specified substance in the form of yellow crystals at a yield of 0.1742 g (yield: 90%)

Sources & evidence

ORD record
ord-de29e2d7be804a69bc4f54071922c49b
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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