Reaktion #81495

Reaktionsgleichung

ethylene oxide

2-fluoro-6-methylpyridine

THF

LDA

→

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

Ausbeute 30.9%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGwith stirring
3. 3
   Extraktionextracted with ether
4. 4
   Waschenthe organic layer was washed with water (2x) and brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   EinengenThe organic solution was concentrated
7. 7
   Sonstigethe residue was purified by flash chromatography (chloroform/ethanol, 10:1)

Vorschrift

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.

Quelle