Reacción #7057

Ecuación de reacción

n-BuLi

3-methoxythiophene

Chlorotrimethylsilane

→

title compound

Rendimiento 82.0%

2-Trimethylsilyl-3-methoxythiophene

Rendimiento 82.0%

Disolventes

Et2O

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is warmed to room temperature
2. 2
   workup.STIRRINGstirred for 3 hr
3. 3
   OtroThe reaction is quenched with water (50 mL) and hexanes (100 mL)
4. 4
   ExtracciónThe aqueous layer is extracted with hexanes (50 mL)
5. 5
   SecadoThe combined organic extracts are dried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude product is chromatographed on silica gel
9. 9
   Lavadoeluting with hexanes

Procedimiento

A solution of n-BuLi (19.7 mL of 1.6 M in hexanes, 31.5 mmol) is added dropwise to a solution of 3-methoxythiophene (3.0 g, 26.3 mmol) in anhydrous Et2O (20 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (4.5 mL, 35.4 mmol) is added slowly to the solution. The mixture is warmed to room temperature and stirred for 3 hr. The reaction is quenched with water (50 mL) and hexanes (100 mL). The aqueous layer is extracted with hexanes (50 mL). The combined organic extracts are dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with hexanes to afford the title compound (4.0 g, 82%) as a colorless liquid.

Fuente