Thiophene → 2,5-Diheptylthiophene

HRID 1720751

Reaktionsgleichung

Reaktionsgleichung von HRID 1720751
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:11][CH2:12][CH2:13]CCC.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:10]([C:2]1[S:1][C:5]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:4][CH:3]=1)[CH2:9][CH2:8][CH2:7][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 8030ThiopheneHCID 8058HexaneHCID 123691-BromoheptaneHCID 178418339Butyllithium

Produkt 1

HCID 6071142,5-DiheptylthiopheneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a typical experiment, 2 g (0.024 mole) of thiophene in 50 ml THF (dried over sodium) were treated with 2.5 eq. 1.5M n-BuLi in hexane (0.06 mole, 45 ml) at 0° C. When addition was completed, the mixture was stirred at room temperature for 5 hours. The solution was cooled at 0° C., quenched with 9.5 ml (0.06 mole) of 1-bromoheptane and then stirred at room temperature for 24 hours. The mixture was poured into ice, extracted with ether, dried (MgSO4), and the solvent evaporated. The crude product contains mono and disubstituted thiophene in the ratio 1:2 (by 1H-nmr). The crude product was then treated under the same conditions as above to yield exclusively 2,5-diheptylthiophene (5.1 g, 76%) bp 225°/0.1 mm. 1H-nmr (CDCl3) shows 86.5 (s, 2H); 2.7 (t, 4H); 0.75-2.0 (M, 26H).

Aufarbeitung

  1. customat 0° C
  2. additionWhen addition
  3. temperatureThe solution was cooled at 0° C.
  4. stirringstirred at room temperature for 24 hours
  5. additionThe mixture was poured into ice
  6. extractionextracted with ether
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. additionThe crude product was then treated under the same conditions as above

Quellen und Nachweise

ORD-Eintrag
ord-53a7dc38df7445789e32d97ca0ce44a8
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506708

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