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

HRID 430734Notizen

Reaktionsgleichung

[CH2:1]1[CH2:9][O:8][C:7]2[C:3](=[CH:4][S:5][CH:6]=2)[O:2]1.C([Li])CCC.[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:4]1[S:5][CH:6]=[C:7]2[O:8][CH2:9][CH2:1][O:2][C:3]=12)[CH2:25][CH2:26][CH3:27]

Komponenten

Reaktionsbedingungen

Temperatur: -40 °C

Versuchsvorschrift

The synthesis described herein is depicted schematically in FIG. 4. 2.0 g (14 mmol) of 3,4-ethylenedioxythiophene in 150 ml dry THF was treated dropwise with 10 ml (16.2 mmol) of 1.6 M n-butyl lithium at −78° C. under argon. After stirring for 0.5 h and warming to −40° C., 5.95 g (18.8 mmol) tributylstannyl chloride was added to the solution and it was warmed to room temperature. The solvent was removed by rotary evaporation after stirring for 8 h. The residue was dissolved in hexanes and filtered. The filtrate was dried in vacuum to afford 6.0 g 2-(tributylstannyl)-3,4-ethylenedioxythiophene as a yellow liquid. The compound was used for next step reaction as obtained, no further purifications. 1H NMR (250 MHZ, CDCl3): d (ppm) 6.56 (s, 1H); 4.16 (s, 4H); 1.61-1.49 (m, 6H); 1.39-1.22 (m, 6H); 1.09 (t, 9H); 0.90 (q, 6H). 13C NMR (125 MHZ, CDCl3): d (ppm) 147.88, 142.65, 109.08, 105.99, 64.86, 64.80, 29.08, 27.40, 13.79, 10.71. (M+H)+ found: 431, caled for C18H32O2SSn: 430.11

Aufarbeitung

temperaturewas warmed to room temperature
customThe solvent was removed by rotary evaporation
stirringafter stirring for 8 h
dissolutionThe residue was dissolved in hexanes
filtrationfiltered
customThe filtrate was dried in vacuum

Quellen und Nachweise

ORD-Eintrag: ord-0e43f0457aba4390adf4b0bd2b7ece16
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06323309B1

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