Reaction #517916

Reaction equation

tributylstannyl chloride

3,4-ethylenedioxythiophene

n-butyl lithium

→

2-(tributylstannyl)-3,4-ethylenedioxythiophene

Yield 99.4%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturewas warmed to room temperature
2. 2
   OtherThe solvent was removed by rotary evaporation
3. 3
   workup.STIRRINGafter stirring for 8 h
4. 4
   workup.DISSOLUTIONThe residue was dissolved in hexanes
5. 5
   Filtrationfiltered
6. 6
   OtherThe filtrate was dried in vacuum

Procedure

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

Source