Propanal → 1055306-54-1

Participants

Reaction Steps

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%).

Provenance & Evidence