Trimethyltin chloride → (5-Hexylthiophen-2-yl)trimethylstannane

HRID 384240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384240
[CH2:1]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li]CCCC.[CH3:17][Sn:18](Cl)([CH3:20])[CH3:19]>C1COCC1>[CH2:1]([C:7]1[S:8][C:9]([Sn:18]([CH3:20])([CH3:19])[CH3:17])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 14016Trimethyltin chlorideHCID 877932-HexylthiopheneHCID 178418339Butyllithium

Produkt 1

HCID 11267529(5-Hexylthiophen-2-yl)trimethylstannane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Hexylthiophene (23.0 g, 0.137 mol) was dissolved in 250 ml THF and n-BuLi (94 ml, 1.6 M in hexanes, 0.150 mol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 h and then cooled down to −78° C. A solution of trimethyltin chloride (32.8 g, 0.164 mol) in 100 ml THF was added dropwise. The mixture was allowed to warm slowly to room temperature and stirred for 2 h. After quenching with ice water and aqueous work-up, the product was distilled at 108° C. under high vacuum. 5-Hexyl-2-trimethylstannylthiophene was obtained as a colourless liquid (40.8 g, 90% yield).

Aufarbeitung

  1. temperaturecooled down to −78° C
  2. temperatureto warm slowly to room temperature
  3. stirringstirred for 2 h
  4. customAfter quenching with ice water and aqueous work-up
  5. distillationthe product was distilled at 108° C. under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2378c8f1859d44b5abecde2703876fa2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367717B2

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