Trimethylsilyl iodide → 3,4-Diphosphonothiophene

HRID 1662876Notes

Reaction equation

HRID 1662876 reaction equation
C([O:3][P:4]([C:9]1[C:13]([P:14]([O:19]CC)([O:16]CC)=[O:15])=[CH:12][S:11][CH:10]=1)([O:6]CC)=[O:5])C.I[Si](C)(C)C>C(#N)C>[P:14]([C:13]1[C:9]([P:4]([OH:5])([OH:6])=[O:3])=[CH:10][S:11][CH:12]=1)([OH:19])([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 59155862HCID 59155862, compound

Product 1

HCID 866384133,4-DiphosphonothiopheneYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile, 0.200 g (0.561 mmols) of 3,4-bis(diethoxyphosphoryl)thiophene was dissolved, to which 0.5613 g (2.805 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 specific substance of white crystals at a yield of 0.1333 g (yield: 97%).

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 specific substance of white crystals at a yield of 0.1333 g (yield: 97%)

Sources & evidence

ORD record
ord-042f5773274e400e94e5243a79bfc8bb
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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