2,5-Difluorobenzaldehyde → HCID 23114690, compound

Participants

Reaction Steps

Lithium diisopropylamide (a 1.8M heptane solution, 12 ml, 21.5 mmol) was added to a tetrahydrofuran (100 ml) solution of 2-(1,3-dioxolan-2-yl)-5-fluoropyridine (690 mg, 4.08 mmol) at −75° C. under an argon atmosphere. The resulting mixture was stirred for 2 hours. To the reaction mixture was added dropwise 2,5-difluorobenzaldehyde (2.1 ml, 19.5 mmol), followed by stirring for 2.5 hours. To the reaction mixture were added water and a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with diethyl ether. The extract was washed with brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=3:1) eluate was concentrated under reduced pressure to give the title compound (2.53 g, 8.03 mmol, 73%) as a white powder.

Provenance & Evidence