反応 #517917

反応方程式

EDOT

nBuLi

Bu3SnCl

→

2-Tributylstannyl-3,4-ethylenedioxythiophene

溶媒

THF

反応条件

後処理

1. 1
   その他The solvent was removed under vacuum
2. 2
   ろ過The slurry was filtered through Celite
3. 3
   その他the amber filtrate was removed under vacuum
4. 4
   その他to yield a yellow-orange oil which
5. 5
   workup.DISTILLATIONwas purified by distillation (b.p. 120° C./30 mTorr)
6. 6
   その他to yield 79.6 g (185, mmol 98%) of pale yellow oil

実験手順

A structure of the product is depicted schematically in FIG. 13. To a cold (−15° C.) solution of 3,4-ethylenedioythiophene (EDOT) (20 ml, 188 mmol) in 350 mL of THF were slowly added 138 mL (207 mmol, 1.1 equiv) of nBuLi. The white slurry was allowed to stir at −15° C. for 3 h before the addition of 61.6 mL (227 mmol, 1.2 equiv) of Bu3SnCl. The beige slurry was allowed to stir while warming to room temperature for 18 h. The solvent was removed under vacuum and then stiffed in hexane for 30 min. The slurry was filtered through Celite and the amber filtrate was removed under vacuum to yield a yellow-orange oil which was purified by distillation (b.p. 120° C./30 mTorr) to yield 79.6 g (185, mmol 98%) of pale yellow oil. 1H NMR (CDCl3) δ6.57 (s, 1H), 4.20-4.10 (m, 4H), 1.62-1.50 (m, 6H), 1.40-1.25 (m, 6H), 1.12-1.06 (m, 6H), 0.89 (t, 3H). MS m/z 433 (M+H+); HRMS (FAB) m/z 433.1225 (M+H+); calcd for C18H32O2SSn m/z 433.1223 (M+H+).

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