Hydrochloric Acid → Dimethyl 2-cyano-3-phenylpentanedioate

Participants

Reaction Steps

To a mixed solution of 5 g of methyl cyanoacetate, 20 mL of methanol, and 20 mL of toluene was added 1.61 g of sodium hydride (55% oil-dispersion) under ice-cooling. After stirring at room temperature for 30 minutes, to the reaction mixture was added 3.24 mL of methyl cinnamate, followed by stirring at 66° C. for 15 hours. The reaction mixture was cooled to room temperature, and 1 M hydrochloric acid was then added thereto to adjust the pH of the solution to about 7. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5.19 g of dimethyl 2-cyano-3-phenylpentanedioate.

Provenance & Evidence