Tributyltin Chloride → Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane

HRID 366859

Reaktionsgleichung

Reaktionsgleichung von HRID 366859
C([Li])CCC.[CH2:6]1[CH2:14][O:13][C:12]2[C:8](=[CH:9][S:10][CH:11]=2)[O:7]1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1[S:10][CH:11]=[C:12]2[O:13][CH2:14][CH2:6][O:7][C:8]=12)[CH2:25][CH2:26][CH3:27]

Komponenten

5

Edukt 3

HCID 15096Tributyltin ChlorideHCID 44218643,4-EthylenedioxythiopheneHCID 178418339Butyllithium

Produkt 1

HCID 15891053Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannaneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

n-Butyllithium (77 mL, 192.5 mmol, 2.5 M solution in hexane) was added dropwise at -78° C. to a solution of 3,4-(ethylenedioxy)thiophene (25 g, 175.9 mmol) in anhydrous THF (100 mL) under nitrogen. The solution was stirred for 1 h and warmed to -40° C. Tributylstannyl chloride (85.89 g, 263.9 mmol) was added and the entire solution was finally allowed to warm to room temperature. At room temperature the mixture was filtered using Celite and the solvent was stripped. The organo-tin compound was vacuum dried to give 2-(tributylstannyl)-3,4-(ethylenedioxy)thiophene, obtained as a dark yellow liquid, yield=98%. MS(EI) m/z (rel int): 375 [(M)+ --C4H8, 100%] and 319[(M)+ --C8H16, 18%].

Aufarbeitung

  1. temperatureto warm to room temperature
  2. filtrationAt room temperature the mixture was filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-891cc2ba15b04d7b843f32e705f27aa2
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130339

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