Sodium Chloride → HCID 54503053, compound

Participants

Reaction Conditions

Reaction Steps

In argon atmosphere, 4.88 g of diisopropylamine was dissolved in 100 ml of dry tetrahydrofuran, followed by dropwise addition of 1.55M n-butyl lithium in 31.1 ml of hexane in solution at -20° C. After stirring at the same temperature for 10 minutes and then cooling down to -78° C., 9.96 g of 2-(3-pyridyl)-2-(trimethylsiloxy)acetonitrile dissolved in 100 ml of dry tetrahydrofuran was added dropwise. After stirring at the same temperature for one hour, 12.99 g of ethyl 4-bromomethylcinnamate dissolved in 100 ml of dry tetrahydrofuran was added, followed by gradual temperature rise from -78° C. to room temperature and stirring overnight. 1.0M Tetra-n-butylammonium fluoride in 48.3 ml of tetrahydrofuran in solution was added and stirred for 3.5 hours. To the reaction mixture was added saturated aqueous sodium chloride solution, and the organic phase was separated, which was then extracted with ethyl acetate from aqueous phase. The organic phases were combined and washed with saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, and 6.21 g of ethyl 4-[2-oxo-2-(3-pyridyl)ethyl]cinnamate was obtained from a fraction eluted with methanol-methylene chloride (2:98 v/v) .

Provenance & Evidence