Convenient syntheses of 4-perfluoroalkyl-6-(α-thienyl)-2-pyranones and methyl 4- (α-thienacyl) -3-perfluoroalkyl-3-butenoates

Add time:08/22/2019    Source:sciencedirect.com

In the presence of K2CO3, reaction of (α-thienacyl)methyltriphenyl phosphonium bromide (1) with methyl 2-perfluoroalkynoates (2) in CH2Cl2 at room temperature gave methyl 4-(α-thienacyl)-2-triphenylphosphoranylidene-3-perfluoroalkyl-3-butenoates (3) in excellent yields. 4-Perfluoroalkyl-6-(α-thienyl)-6-pyranones (4) and methyl 4-(α-thienacyl)-3-perfluoroalkyl-3-butenoates (5) were obtained in high yield by hydrolysis of these methylene phosphoranes (3) with hot aqueous methanol. The butenoates (5) were isolated chromatographically as mixtures of Z and E isomers, the ratios of which were estimated by 1H NMR. Reaction mechanisms are proposed to account for the formation of products 3, 4 and 5.

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