Diisopropylamine → 3-Chloro-4-[(2,5-difluorophenyl)-hydroxymethyl]pyridine

Participants

Reaction Conditions

Reaction Steps

To a tetrahydrofuran solution (14 ml) of diisopropylamine (1.4 ml, 10 mmol) was added n-butyl lithium (6.3 ml, a 1.59M hexane solution) at −78° C. After the resulting mixture was stirred for 10 minutes, 3-chloropyridine (1.13 g, 10 mmol) was added thereto. Thirty minutes later, 2,5-difluorobenzaldehyde (1.09 ml, 10 mmol) was added and the temperature of the resulting mixture was raised gradually to 0° C. Stirring was conducted for further 10 minutes. After addition of an aqueous solution of ammonium chloride, the resulting mixture was diluted with ethyl acetate (80 ml). The organic layer was separated, washed with brine and then dried. After filtration, the precipitate obtained by concentrating the resulting solution under reduced pressure was triturated with ethanol to give the title compound (1.33 g, 52%).

Provenance & Evidence