反应 #81495

反应方程式

ethylene oxide

2-fluoro-6-methylpyridine

THF

LDA

→

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

收率 30.9%

溶剂

water

反应条件

后处理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGwith stirring
3. 3
   萃取extracted with ether
4. 4
   洗涤the organic layer was washed with water (2x) and brine
5. 5
   干燥dried over sodium sulfate
6. 6
   浓缩The organic solution was concentrated
7. 7
   其他the residue was purified by flash chromatography (chloroform/ethanol, 10:1)

实验过程

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.

来源