Реакция #156175

Уравнение реакции

Water

Sodium hydride

6-Hydroxy-2-methoxyquinoline

1,8-Dibromooctane

→

title compound

6-(8-bromooctyloxy)-2-methoxyquinoline

Растворители

—

ice water

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   Экстракцияfollowed by extraction
3. 3
   СушкаThe organic layer was dried with sodium sulfate
4. 4
   Другоеcondensed under reduced pressure
5. 5
   ДругоеThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)
6. 6
   Другоеcondensed to dryness under reduced pressure

Методика

Sodium hydride (60% in oil, 40 mg) was suspended in DMF (2 ml), and was cooled to 0° C. in ice water bath. 6-Hydroxy-2-methoxyquinoline (171 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. 1,8-Dibromooctane (0.37 ml) was added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1). The purified product was condensed to dryness under reduced pressure to give the title compound (225 mg) as a white powder.

Источник