Friedel–Crafts Reaction of Activated Benzene Rings with Captodative and Electron‐Deficient Alkenes. A One‐Step Synthesis of the Natural Product Methyl 3‐(2,4,5‐Trimethoxyphenyl)propionate

Abstract

Abstract Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1‐acetylvinyl‐1‐p‐nitrobenzoate (9), and with the electron‐deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a–8c. We also describe a one‐step synthesis of the antifungal and larvicidal natural product methyl 3‐(2,4,5‐trimethoxyphenyl)propionate (6), by reaction of 1,2,4‐trimethoxybenzene with 8a under microwave irradiation.