Ethylene Oxide → 6-Fluoro-2-pyridinepropanol

Temperature

-78 °C

To a solution of 2-fluoro-6-methylpyridin (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 which stirring. The mixture was diluted with water, extracted with ether, and the organic layer was washed with water (2×) 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.

1. temperatureto warm to room temperature which
2. stirringstirring
3. extractionextracted with ether
4. washthe organic layer was washed with water (2×) and brine
5. dry with materialdried over sodium sulfate
6. concentrationThe organic solution was concentrated
7. customthe residue was purified by flash chromatography (chloroform/ethanol, 10:1)

ORD record

ord-a40c09c9f82c43a7b1fa57d35d1dc6a0

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763461