反応 #59910

反応方程式

(1-methyl-2,6,7-trioxabicyclo[2.2.2]oct-4-yl)methanol

sodium hydride

4-chloro-2,3-dimethylpyridine 1-oxide

→

title compound

収率 104.8%

2,3-dimethyl-4-((1-methyl-2,6,7-trioxabicyclo[2.2.2]oct-4-yl)methoxy)pyridine1-oxide

収率 104.8%

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   温度After cooled to room temperature
3. 3
   濃縮the reaction mixture was concentrated under reduced pressure
4. 4
   その他The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol)

実験手順

To a dimethylsulfoxide solution (30 ml) of the (1-methyl-2,6,7-trioxabicyclo[2.2.2]oct-4-yl)methanol (4.5 g, 28.1 mmol) obtained in the step (24a), sodium hydride, in oil (1.29 g, 29.5 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (3.99 g, 25.3 mmol) was added, which was stirred at 60° C. for 3 hours. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol) to obtain the title compound (7.46 g, yield: 81%) as a yellow oil.

出典