反応 #59866

反応方程式

(8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methanol

sodium hydride

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

→

title compound

収率 66.2%

2,3-dimethyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridine1-oxide

収率 66.2%

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   workup.ADDITIONwas added at room temperature in a nitrogen atmosphere
2. 2
   workup.STIRRINGthe reaction mixture was stirred at 70° C. for 4.5 hours
3. 3
   濃縮The reaction mixture was concentrated
4. 4
   その他the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-5/2 gradient)
5. 5
   濃縮desired fractions were concentrated

実験手順

To a dimethylsulfoxide (15 ml) solution of the (8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methanol (1.11 g, 5.82 mmol) obtained in the step (5c), sodium hydride, in oil (326 mg, 8.15 mmol as the content was regarded as 60%) was added at room temperature in a nitrogen atmosphere. The mixture was stirred for 30 minutes in the same conditions. To the reaction mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (917 mg, 5.82 mmol) was added at room temperature and the reaction mixture was stirred at 70° C. for 4.5 hours. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-5/2 gradient) and desired fractions were concentrated to obtain the title compound (1.20 g, 66.1% yield) as a brown oil.

出典