Reaktion #7057

Reaktionsgleichung

n-BuLi

3-methoxythiophene

Chlorotrimethylsilane

→

title compound

Ausbeute 82.0%

2-Trimethylsilyl-3-methoxythiophene

Ausbeute 82.0%

Lösungsmittel

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is warmed to room temperature
2. 2
   workup.STIRRINGstirred for 3 hr
3. 3
   SonstigeThe reaction is quenched with water (50 mL) and hexanes (100 mL)
4. 4
   ExtraktionThe aqueous layer is extracted with hexanes (50 mL)
5. 5
   TrocknenThe combined organic extracts are dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product is chromatographed on silica gel
9. 9
   Wascheneluting with hexanes

Vorschrift

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.

Quelle