Reaction #517917

Reaction equation

EDOT

nBuLi

Bu3SnCl

→

2-Tributylstannyl-3,4-ethylenedioxythiophene

Solvents

THF

Conditions

Workup

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

Procedure

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+).

Source