Reacción #1838501

Ecuación de reacción

tributylstannyl chloride

EDOT

THF

LDA

→

oil 6

Rendimiento 92.0%

2,5-bis(tributylstannyl)-3,4-ethylenedioxythiophene

Rendimiento 92.0%

Disolventes

water ethylacetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to 0
2. 2
   workup.ADDITIONafter addition
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGby stirring at 0 for 1 hour
5. 5
   OtroAn organic layer was separated from the reactant
6. 6
   Lavadothe separated organic layer was washed with water
7. 7
   Secadolastly dried with anhydrous sodium sulfate
8. 8
   OtroThe solvent was evaporated under reduced pressure
9. 9
   Otrothus-obtained residues
10. 10
    Otrowere purified by flash chromatography
11. 11
    workup.ADDITIONpre-treated with triethylamine

Procedimiento

EDOT (5, 1.42 g, 10 mmol) was dissolved into anhydrous THF (40 ml) and cooled to 0. After stirring at 0 for 15 minutes, LDA (15 mL, 2M, THF/heptane/ethylebenzene) was added for 15 minutes, and after addition was complete, a reaction mixture was heated to room temperature for 1 hour. The reaction mixture was cooled to 0 and tributylstannyl chloride (8.1 ml, 30 mmol) was added thereto, followed by stirring at 0 for 1 hour, and water ethylacetate were added thereto. An organic layer was separated from the reactant and the separated organic layer was washed with water and lastly dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and thus-obtained residues were purified by flash chromatography using hexane as eluent in silica gel pre-treated with triethylamine to obtain a colorless oil 6 (6.61 g, 92%). 1H NMR (CDCl3, 400 MHz, d/ppm): 4.03-4.02 (d, J=4 Hz, 4H2OCH2CH2O), 1.60-1.40 (m, 12, 2×Sn—(CH2—)3), 1.26-1.20 (m, 12H, 2×Sn—(CH2CH2—)3), 1.00 (m, 12H, 2×Sn—(CH2CH2CH2—)3), 0.83-0.79 (m, 18H, 2×(CH3)3). 13C NMR (CDCl3, 100 MHz, d/ppm): 148.29, 115.81, 64.62, 29.01, 27.20, 13.69, 10.48. C30H58O2SSn2 (720.27): Theoretical value C, 50.03; H, 8.12; S, 4.45; Sn, 32.96; Experimental value C, 50.18; H, 8.08; S, 4.39.

Fuente