反応 #81495

反応方程式

ethylene oxide

2-fluoro-6-methylpyridine

THF

LDA

→

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

収率 30.9%

溶媒

water

反応条件

後処理

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

実験手順

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.

出典