Photochemical Transformation of Methyl Coumalate
This application note illustrates the use of the Vapourtec UV-150 photochemical reactor which allows access to continuous photochemistry in an easy-to-use, safe and efficient manner.
Considering the lamp as a fixed flux of photons (photons/min) the flow rate and concentration of the reagent will therefore have a direct effect on the stoichiometry of the reaction and therefore theconversion and yield of any photochemical reaction.
The photochemical transformation of methyl coumalate to the pyrone via electrocyclisation has been shown in the total synthesis of a range of Piperarborenines by Prof. Phil Baran’s group1,2. Baran et al performed the photochemical reaction under traditional batch conditions irradiating his reaction in a jacketed quartz immersion well with a pyrex filtered 450W mercury lamp. Studies carried out by Prof.
Reva show this transformation to be wavelength dependant with wavelengths >295nm necessary to prevent side reactions occurring 3.
Background
Continuous flow chemistry offers easy access to scaling reactions from milligrams to kilograms, and many successful examples have been well documented. The Vapourtec UV-150 photochemical reactor extends these advantages by giving the chemist easy access to continuous photochemical reactions. Photochemistry is a valuable but underused synthetic tool and offers potentially shorter and more efficient synthetic routes as well as access to new chemical space.
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