반응 #7057

반응 방정식

n-BuLi

3-methoxythiophene

Chlorotrimethylsilane

→

title compound

수율 82.0%

2-Trimethylsilyl-3-methoxythiophene

수율 82.0%

용매

Et2O

반응 조건

후처리

1. 1
   온도The mixture is warmed to room temperature
2. 2
   workup.STIRRINGstirred for 3 hr
3. 3
   기타The reaction is quenched with water (50 mL) and hexanes (100 mL)
4. 4
   추출The aqueous layer is extracted with hexanes (50 mL)
5. 5
   건조The combined organic extracts are dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude product is chromatographed on silica gel
9. 9
   세척eluting with hexanes

실험 절차

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.

출처