Ethylene Oxide → 3-(3-Cyanopyridin-4-yl)-1-propanol

Temperature

20 °C

Diisopropylamine (2.5 g, 25 mmol) is dissolved in THF (30 ml), and thereto is added a solution of n-butyl lithium in hexane (14.3 ml, 24 mmol) at −70° C. The mixture is stirred for 15 minutes, and thereto is added a solution of 3-cyano-4-methylpyridine (2.4 g, 20 mmol) obtained in Reference Example 33 in THF (20 ml). Ten minutes thereafter, ethylene oxide (1.1 g, 24 mmol) is added to the mixture, and the mixture is warmed to 20° C. over a period of time for one hour. The reaction is quenched with a saturated brine (50 ml), and the mixture is extracted with ethyl acetate (150 ml×2). The organic layer is washed with a saturated brine (100 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give the title compound (1.2 g) as a pale brown oil.

1. customThe reaction is quenched with a saturated brine (50 ml)
2. extractionthe mixture is extracted with ethyl acetate (150 ml×2)
3. washThe organic layer is washed with a saturated brine (100 ml×2)
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD record

ord-c0bc4df97ed64a1b9826e7a26437c3bd

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06683186B2