Reaction #81495

Reaction equation

ethylene oxide

2-fluoro-6-methylpyridine

THF

LDA

→

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

Yield 30.9%

Solvents

water

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   workup.STIRRINGwith stirring
3. 3
   Extractionextracted with ether
4. 4
   Washthe organic layer was washed with water (2x) and brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   ConcentrationThe organic solution was concentrated
7. 7
   Otherthe residue was purified by flash chromatography (chloroform/ethanol, 10:1)

Procedure

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.

Source