MATERIALS AND METHODS FOR THE BASE-ASSISTED SYNTHESIS OF SUBSTITUTED HETEROAROMATIC COMPOUNDS

摘要

Disclosed herein are some methods for synthesizing the base-assisted coupling of aromatic alcohols with substituted aromatic compounds including some substituted heteroaromatic compounds such as pyrimidines or pyridines to form esters. The reactions may include inexpensive bases such as potassium hydroxide and take place in a solvent mixture comprised primarily of hindered tertiary alcohols that are at least partially immiscible with water. In some embodiments the tertiary alcohol solvents forms azeotropes with water which stabilize the formation of an alkoxide intermediate when the alkoxide formation step is heated to the boiling point of the azeotrope and water is withdrawn from the reaction mixture.

主权项

1. A method for conducting base-assisted reactions, comprising the steps of:
forming an alkoxide by:
mixing at least one alcohol with at least one metal hydroxide in the presence of a tertiary alcohol, wherein said tertiary alcohol is at least partially immiscible with water; contacting said alkoxide with an aromatic compound, wherein a halogen substituted aromatic compound, and wherein the halogen substituted aromatic compound undergoes a base-assisted coupling with said alkoxide to form an ether.