Acetone → 2-(2-Fluoropyridin-3-yl)ethanol

A solution of 2.0 g (20.6 mmol) of 2-fluoropyridine in 25 ml of dry THF was cooled to -78° C. was added 25 ml (1.6M in hexanes, 41.6 mmol) n-BuLi under an atmosphere of nitrogen. The mixture was stirred at this temperature for 2 hours before an addition of 4 ml ethylene oxide in 7 ml ether. The mixture was warmed to room temperature, 150 ml ether and 25 ml acetone was added. The precipitate was removed by filtration, and the filtrate was concentrated to 1/3 of volume in vacuo. The remainder was washed once with brine, dried with Na2SO4, and concentrated in vacuo. The crude material was purified by dry column flash chromatography (hexane/EtOAc) to afford 0.42 g of 3-(2-hydroxyethyl)-2-fluoropyridine as a brown oil.

1. customThe precipitate was removed by filtration
2. concentrationthe filtrate was concentrated to 1/3 of volume in vacuo
3. washThe remainder was washed once with brine
4. dry with materialdried with Na2SO4
5. concentrationconcentrated in vacuo
6. customThe crude material was purified
7. dry with materialby dry column flash chromatography (hexane/EtOAc)

ORD record

ord-2cb8c5a5e8f34d0d9fcc73736fbc2b85

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05593993