Реакция #81495

Уравнение реакции

ethylene oxide

2-fluoro-6-methylpyridine

THF

LDA

→

2-fluoro-6-(3-hydroxypropyl)pyridine

Выход 30.9%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураto warm to room temperature
2. 2
   workup.STIRRINGwith stirring
3. 3
   Экстракцияextracted with ether
4. 4
   Промывкаthe organic layer was washed with water (2x) and brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   КонцентрированиеThe organic solution was concentrated
7. 7
   Другоеthe residue was purified by flash chromatography (chloroform/ethanol, 10:1)

Методика

To a solution of 2-fluoro-6-methylpyridine (27 mmol) in 65 ml of freshly distilled THF was added via syringe 13.5 ml of 2M LDA, and the resulting mixture was stirred at -78° C. for 20 min. To the above cold solution was added 4 ml of 4M ethylene oxide and the mixture was allowed to warm to room temperature with stirring. The mixture was diluted with water, extracted with ether, and the organic layer was washed with water (2x) and brine, and dried over sodium sulfate. The organic solution was concentrated, and the residue was purified by flash chromatography (chloroform/ethanol, 10:1) to yield 1.3 g (30.9%) of 2-fluoro-6-(3-hydroxypropyl)pyridine, as a yellow oil.

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