3-Pyridinecarboxaldehyde → HCID 12904596, compound

Participants

Reaction Steps

To a solution of 1.88 g of 4 -bromo-3-methylbenzaldehyde diethylacetal in 20 ml of diethyl ether was added dropwise 5.0 ml of a 1.4M solution of butyllithium in hexane at -70° C. to 0° C., and the mixture was stirred at 0° C. to -50° C. for 50 minutes. To it was added dropwise 0.89 g of 3-formylpyridine at -30° C. to -20° C., and the reaction mixture allowed to warm to room temperature with stirring. After concentration under reduced pressure the residue was stirred with 10 ml of tetrahydrofuran and 10 ml of 2N hydrochloric acid at room temperature for 45 minutes. The reaction mixture was basified with sodium bicarbonate, extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:2) as eluent to give 1.20 g of the title compound having the following physical characteristics:

Provenance & Evidence