3-Pyridinecarboxaldehyde → HCID 53866777, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.95 g of 4-bromothiophenol in 20 ml of tetrahydrofuran was added dropwise to 7.5 ml of a 1.4 M solution of butyllithium in hexane at -70° to -60° C. After allowed to warm to 0° C., the mixture was stirred at 0° C. for 5 minutes. To it was added a solution of 0.505 g of 3-formylpyridine in 10 ml of tetrahydrofuran at -70° C., and the mixture was stirred at -70° C. for 30 minutes. To the mixture was added 0.91 g of 2-bromopropionic acid ethyl ester at -70° C., and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, 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 (1:4) as eluent to give 0.66 g of the title compound having the following physical characteristic:

Provenance & Evidence