Diethyl Malonate → Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate

Participants

Reaction Conditions

Reaction Steps

To a solution of this aldehyde (10.0 g, 60.6 mmol) in 20 mL of acetic anhydride was added diethyl malonate (9.7 g, 60.6 mmol) and sodium bicarbonate (7.6 g, 91 mmol). The reaction mixture was stirred at 100° C. for 24 h. The reaction was allowed to cool and then was partitioned between ethyl acetate and water. The organics were washed sequentially with water, aq sat'd NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 16.9 g (90%) of the title compound.

Provenance & Evidence