2-(Tri-n-butylstannyl)thiophene → 3-Diethoxyphosphoryl-[2,2']-bithiophene

HRID 1662897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662897
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Sn](CCCC)(CCCC)CCCC.I[C:20]1[S:21][CH:22]=[CH:23][C:24]=1[P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26]>O1CCCC1.[Cu]Cl>[CH2:28]([O:27][P:25]([C:24]1[CH:23]=[CH:22][S:21][C:20]=1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([O:30][CH2:31][CH3:32])=[O:26])[CH3:29]

Komponenten

5

Edukt 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 591558362-Iodo-3-diethoxyphosphorylthiophene

Produkt 1

HCID 591558283-Diethoxyphosphoryl-[2,2']-bithiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Copper(I) chloride (2.5 equivalents) was charged into a reaction container, to which 2-thienyltributyl tin (2.5 equivalents) and 2-iodo-3-diethoxyphosphorylthiophene were added under nitrogen atmosphere while being dissolved in tetrahydrofuran, followed by heating under reflux for 20 hours. After completion of the reaction, the reaction solution was filtered through celite and the resulting residue was washed with ethyl acetate. The filtrate was washed three times with a 1N hydrochloric acid aqueous solution and a 10% saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting crude product was purified with a silica gel column (hexane:ethyl acetate=1:3) to obtain a colorless liquid.

Aufarbeitung

  1. additionwere added under nitrogen atmosphere
  2. temperatureby heating
  3. temperatureunder reflux for 20 hours
  4. customAfter completion of the reaction
  5. filtrationthe reaction solution was filtered through celite
  6. washthe resulting residue was washed with ethyl acetate
  7. washThe filtrate was washed three times with a 1N hydrochloric acid aqueous solution
  8. dry with materiala 10% saline solution and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe resulting crude product was purified with a silica gel column (hexane:ethyl acetate=1:3)
  11. customto obtain a colorless liquid

Quellen und Nachweise

ORD-Eintrag
ord-2055e280654845ffbbfc71d2e378ae04
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030438B2

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