Propanal → 3-Pyridinemethanol, alpha-ethyl-2-fluoro-

To a solution of diisopropylamine (15.8 g) in tetrahydrofuran (100 mL) was added dropwise a 1.6 mol/L hexane solution (95 mL) of n-butyllithium at −78° C., and the mixture was stirred for 15 min. A solution of 2-fluoropyridine (11.6 g) in tetrahydrofuran (10 mL) was added dropwise at −78° C., and the mixture was stirred at the same temperature for 30 min. To the obtained mixture was added a solution of propionaldehyde (11.2 mL) in tetrahydrofuran (10 mL) at the same temperature, and the mixture was further stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1) to give the title compound as a brown oil (yield 12.4 g, 67%).

1. stirringthe mixture was stirred at the same temperature for 30 min
2. stirringthe mixture was further stirred for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1)

ORD-Eintrag

ord-b34b1cb4dbbb4ec79530a8e7d3e12b01

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08933105B2