Question

In the following reaction the cyanoacetate is first treated with methoxide and then slowly added to the aldehyde under heated conditions. Draw the structure of the major product.

In the following reaction the cyanoacetate is first treated with methoxide and then slowly added to the aldehyde under heated conditions. Draw the structure of the major product.

Answer 1

Treatment of methyl 2-cyanoacetate with a strong base, methoxide ion, forms a resonance-stabilized enolate ion, which further reacts with furan-2-carbaldehyde followed by the hydrolysis gives methyl 2-cyano-3-(furan-2-yl)-3-hydroxypropanoate. Now, the formed undergoes dehydration in the presence of heat to form the (E)-methyl 2-cyano-3- (furan-2-y)acrylate. Thus, the reaction is as follows CH3O CH3OH methyl 2-cyanoacetate H20 heat он

Answer 2