Réaction #7057

Équation de réaction

n-BuLi

3-methoxythiophene

Chlorotrimethylsilane

→

title compound

Rendement 82.0%

2-Trimethylsilyl-3-methoxythiophene

Rendement 82.0%

Solvants

Et2O

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is warmed to room temperature
2. 2
   workup.STIRRINGstirred for 3 hr
3. 3
   AutreThe reaction is quenched with water (50 mL) and hexanes (100 mL)
4. 4
   ExtractionThe aqueous layer is extracted with hexanes (50 mL)
5. 5
   SéchageThe combined organic extracts are dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude product is chromatographed on silica gel
9. 9
   Lavageeluting with hexanes

Mode opératoire

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.

Source