Veratryl chloride → Ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate

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Reaction Steps

A solution of 9.9 g of ethyl 4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate in 40 ml of absolute ethanol is added to a solution of 0.9 g of sodium in 50 ml of absolute ethanol at room temperature with stirring. The stirring is continued for one hour. To the mixture is added 8 g of 3,4-dimethoxybenzyl chloride. The resulting mixture is held at room temperature with stirring for one hour and then refluxed for an additional two hours. The ethanol is then removed under reduced pressure, water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from ethanol to give 11.5 g of ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate, melting at 167°-168°C.

Provenance & Evidence