The reaction of diethyl malonate with sodium ethyl glycolate

Diethyl malonate is mild and famous in the field of organic synthesis. Sodium glycolate is a strong base with active chemical properties. When the two meet, a wonderful chemical reaction is initiated.

When diethyl malonate is mixed with sodium glycolide, the negative charge of ethoxyl in sodium glycolide shows a strong attraction to the α-hydrogen of the ester group in diethyl malonate. This α-hydrogen is affected by the ester group and has a certain acidity, which is easier to be taken away. Sodium ethyl alcohol decisively grabs the alpha-hydrogen, causing the formation of a carboanion at the alpha-carbon of diethyl malonate.

This carboanion is extremely active, like a wanderer eagerly seeking a home. It has strong nucleophilic properties and is prone to attack many electrophilic reagents. If there are suitable halogenated hydrocarbons in the system, this carboanion will attack the carbon-halogen bond of the halogenated hydrocarbon hungrily. The halogen atom carries electrons away, forming a new carbon-carbon bond, resulting in a substituted diethyl malonate derivative.

If the conditions are suitable and the halogenated hydrocarbons are sufficient, this reaction can be further advanced. One of the substituted derivatives has been formed, and the remaining α-hydrogen can still be taken away under the action of sodium ethanol, forming a carbon negative ion again. The carbon negative ion reacts with halogenated hydrocarbons according to the same mechanism, and then generates a dissubstituted diethyl malonate derivative.

This reaction is of great significance in organic synthesis. By cleverly selecting halogenated hydrocarbons, a rich and diverse carbon skeleton structure can be precisely constructed, laying a solid foundation for the preparation of various carboxylic acids and their derivatives. With their in-depth understanding and delicate regulation of this reaction, chemists have drawn a colorful chemical blueprint in the vast world of organic synthesis, promoting the discipline of organic chemistry to new heights.