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

HRID 1662878Notes

Reaction equation

HRID 1662878 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][C:24]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[CH:25][CH:26]=2)[S:11][C:10]=1[C:32]1[S:36][C:35]([C:37]2[S:38][CH:39]=[CH:40][CH:41]=2)=[CH:34][CH:33]=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:19])([OH:16])=[O:15])=[C:12]([C:22]2[S:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[CH:25][CH:26]=2)[S:11][C:10]=1[C:32]1[S:36][C:35]([C:37]2[S:38][CH:39]=[CH:40][CH:41]=2)=[CH:34][CH:33]=1)([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 591559243'',4''-Bis(diethoxyphosphoryl)-[2,2';5',2'';5'',2''';5''',2'''']-quinquethiophene

Product 1

HCID 591558763'',4''-Diphosphono-[2,2';5',2'';5'',2''';5''',2'''']-quinquethiopheneYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 4.0 ml of acetonitrile, 0.2746 g (0.401 mmols) of 3″,4″-bis(diethoxyphosphoryl)-[2,2′;5′,2″;5″,2″′;5″′,2″″]-quinquethiophene was dissolved, to which 0.4012 g (2.005 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. A sodium thiosulfate aqueous solution was added, followed by stirring, filtration of the precipitated crystals, washing with distilled water, methanol, chloroform and diethyl ether and drying to obtain the specified substance in the form of a yellow powder at a yield of 0.1630 g (yield: 71%).

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. additionA sodium thiosulfate aqueous solution was added
  8. stirringby stirring
  9. filtrationfiltration of the precipitated crystals
  10. washwashing with distilled water, methanol, chloroform and diethyl ether
  11. customdrying
  12. customto obtain the specified substance in the form of a yellow powder at a yield of 0.1630 g (yield: 71%)

Sources & evidence

ORD record
ord-b05147d46ffb4d2ba5172cda13223006
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

Loading…