反応 #6224

反応方程式

4-hydroxypyridine

N-chloromethylphthalimide

1,8-diazabicyclo[5,4,0]-7-undecene

→

desired compound

収率 21.0%

4-(phthalimidomethyloxy)pyridine

収率 21.0%

溶媒

DMF

反応条件

後処理

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe reaction mixture was poured into water
3. 3
   抽出extracted with ethyl acetate
4. 4
   ろ過The precipitate was filtered off
5. 5
   抽出The aqueous layer was further extracted with ethyl acetate
6. 6
   洗浄The organic layer was washed with water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   その他The residue was purified by column chromatography (eluent: ethyl acetate)

実験手順

To a solution of 4.76 g (50 mmol) of 4-hydroxypyridine and 10.76 g (55 mmol) of N-chloromethylphthalimide in 80 ml of DMF, 8.23 ml (55 mmol) of 1,8-diazabicyclo[5,4,0]-7-undecene was added. The mixture was stirred at room temperature for 2 hours. After the solvent was distilled off, the reaction mixture was poured into water and extracted with ethyl acetate. The precipitate was filtered off. The aqueous layer was further extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 2.67 g of the desired compound (yield: 21%, colorless crystals).

出典