Diethyl malonate reaction
Diethyl malonate, its agility, in the field of organic synthesis, play a great role.
Diethyl malonate has active methylene, this methylene is affected by carbonyl on both sides, and the hydrogen atom is acidic. In case of strong bases, such as sodium alcohol, methylene hydrogen is easy to leave, generating stable carbon negative ions. This carbon negative ion, like a smart messenger, can be replaced with halogenated hydrocarbons nucleophilic. Halogenated hydrocarbons are diverse, or primary halogenated hydrocarbons, or have special structures. After the reaction, the carbon chain ingeniously grows. The resulting products can be hydrolyzed and decarboxylated to obtain various carboxylic acids. This is an exquisite way to construct carboxylic acids.
And diethyl malonate can also dance with aldose and ketone. Under the catalysis of alkali, carbon negative ions are nucleophilic added to aldose and ketone carbonyl to form key intermediates. After a series of transformations, or acidification, or dehydration, etc., a variety of oxygen-containing heterocyclic compounds can be produced, or alcohols, aldose, and ketones with special structures can be generated.
Furthermore, the reaction involving diethyl malonate can be carried out under mild conditions, and it also needs fine regulation. Temperature, solvent, and the proportion of reactants are all like silk threads, which affect the direction of the reaction. The appropriate temperature may promote the efficient progress of the reaction, or guide the reaction to the desired product. The nature of the solvent also affects the reaction rate and selectivity.
In summary, diethyl malonate, with its unique reaction properties, weaves a beautiful picture of thousands of compounds on the stage of organic synthesis, paving a solid way for the development of organic chemistry.