… (Z)-α, β-difluoroallyl alcohols and (Z)-α-fluoro-α, β-unsaturated aldehydes based on the reaction of 2, 3, 3-trifluoro-1-propenyl p-chlorobenzenesulfonate with Grignard …

K Funabiki, Y Fukushima, T Inagaki, E Murata…

Index: Funabiki, Kazumasa; Fukushima, Yoshitaka; Inagaki, Tomomi; Murata, Eiji; Matsui, Masaki; Shibata, Katsuyoshi Tetrahedron Letters, 1998 , vol. 39, # 14 p. 1913 - 1916

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Citation Number: 16

Abstract

2, 3, 3-Trifluoro-1-propenyl p-chlorobenzenesulfonate (1), readily available from 2, 2, 3, 3- tetrafluoropropanol, reacted smoothly with various Grignard reagents at 50° C to afford the corresponding (Z)-α, β-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed in the presence of a catalytic amount of montmorillonite K10 (Clay) to provide (Z)-α-fluoro-α, β-unsaturated aldehydes 3 in good yields.