Reaktion #954579

Reaktionsgleichung

water

magnesium

2-ethoxy-5-bromopyridine

chlorodimethylsilane

→

2-ethoxy-5-dimethylsilylpyridine

Ausbeute 43.0%

Lösungsmittel

THF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea strongly exothermic reaction
2. 2
   Temperaturby refluxing for two hours
3. 3
   Extraktionextracted repeatedly with n-hexane
4. 4
   WaschenThe extracts are washed with water and saturated sodium chloride solution
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   workup.DISTILLATIONthe residue is distilled

Vorschrift

A mixture of 18.2 g (0.09 mol) of 2-ethoxy-5-bromopyridine (can be obtained from 2,5-dibromopyridine and sodium methanolate in DMSO), 11.4 g (0.12 mol) of chlorodimethylsilane and 50 ml of anhydrous tetrahydrofuran (THF) is added dropwise to 2.4 g (0.10 mol) of magnesium turnings in 10 ml of anhydrous THF, a strongly exothermic reaction occurring. The reaction is completed by refluxing for two hours. The mixture is then poured into water and extracted repeatedly with n-hexane, The extracts are washed with water and saturated sodium chloride solution, dried and evaporated, and the residue is distilled. 7 g (43%) of 2-ethoxy-5-dimethylsilylpyridine are obtained as a colorless oil of boiling point 7=140°-150° C.

Quelle