Hexane → [4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']bisthiene-2,6-diyl]bis(trimethylstannane)

HRID 1897396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1897396
[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][C:5]1([CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[C:7]2[S:8][CH:9]=[CH:10][C:6]1=2)[CH3:2].[Li]CCCC.[CH2:33]([Sn:37](Cl)([CH2:42]CCC)[CH2:38]CCC)CCC.CCCCCC>C1COCC1>[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][C:5]1([CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[C:6]2[CH:10]=[C:9]([Sn:37]([CH3:42])([CH3:38])[CH3:33])[S:8][C:7]=2[C:11]2[S:12][C:13]([Sn:37]([CH3:42])([CH3:38])[CH3:33])=[CH:14][C:15]1=2)[CH3:2]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 59426893HCID 59426893, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 44203213[4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']bisthiene-2,6-diyl]bis(trimethylstannane)Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (3.0 g, 7.45 mmol) prepared above was dissolved in anhydrous THF (20 mL) and kept at −78° C. under nitrogen flow. Then, n-BuLi (19 mL, 29.8 mmol, 2.5 M in hexane) was slowly added over 30 minutes. Subsequently, after stirring at −78° C. for 1 hour, tributyltin chloride (7.4 g, 37.1 mmol) was added and reaction was performed at room temperature for 17 hours. The resulting product was extracted with ether and distilled water, dried with anhydrous MgSO4 and filtered under reduced pressure. The final product 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (5.1 g, yield: 94%) was obtained by column chromatography (neutral alumina, n-hexane). 1H NMR (300 MHz, CDCl3, ppm): δ 7.01-6.88 (m, 2H), 1.93-1.76 (m, 4H), 1.04-0.81 (m, 18H), 0.74 (t, 6H), 0.59 (t, 6H), 0.49-0.22 (m, 18H).

Aufarbeitung

  1. customkept at −78° C. under nitrogen
  2. customreaction
  3. waitwas performed at room temperature for 17 hours
  4. extractionThe resulting product was extracted with ether
  5. distillationdistilled water
  6. dry with materialdried with anhydrous MgSO4
  7. filtrationfiltered under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-285defcc70a34d9096be0fc79034af18
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519087B2

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