تفاعل #6224

معادلة التفاعل

4-hydroxypyridine

N-chloromethylphthalimide

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

→

desired compound

المردود 21.0%

4-(phthalimidomethyloxy)pyridine

المردود 21.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONthe reaction mixture was poured into water
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   ترشيحThe precipitate was filtered off
5. 5
   استخلاصThe aqueous layer was further extracted with ethyl acetate
6. 6
   غسيلThe organic layer was washed with water
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   أخرىThe residue was purified by column chromatography (eluent: ethyl acetate)

الإجراء التجريبي

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).

المصدر