Process for producing vinyl perfluoroalkanesulfonate derivative

C - Chemistry – Metallurgy – 07 – C

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C07C 303/26 (2006.01) C07C 309/65 (2006.01) C07J 31/00 (2006.01)

Patent

CA 2490715

A process for producing easily and at a low cost vinyl perfluoroalkanesulfonate derivatives of the general formula (IV) useful as intermediates in the synthesis of drugs, natural products, and so on, characterized by reacting a carbonyl compound of the general formula (I) with a perfluoro- alkanesulfonic anhydride of the general formula (II) in the presence of 0.1 to 1.0 equivalent of a pyridine derivative of the general formula (III) based on the perfluoroalkanesulfonic anhydride. (A) (In the scheme, R1, R2, R3, R4, and R5 are each independently hydrogen, optionally substituted lower alkyl, optionally substituted lower alkoxy, or the like; R17 is trifluoromethyl or the like; and R18, R19, R20, R21, and R22 are each independently hydrogen, optionally substituted lower alkyl, or the like.)

L'invention concerne un procédé qui permet de produire facilement et à bas prix des dérivés de perfluoroalcanesulfonate de vinyle de formule générale (IV), utiles comme intermédiaires dans la synthèse de médicaments, de produits naturels, etc. Le procédé consiste à mettre en réaction un composé carbonyle de formule générale (I) avec de l'anhydride perfluoroalcanesulfonique de formule générale (II), en présence de 0,1 à 1,0 équivalent d'un dérivé de pyridine de formule générale (III), sur la base de l'anhydride perfluoroalcanesulfonique. Dans la formule (A), R?1¿, R?2¿, R?3¿, R?4¿ et R?5¿ sont chacun, indépendamment, hydrogène, alkyle inférieur éventuellement substitué, alcoxy inférieur éventuellement substitué ou analogue; R?17¿ est trifluorométhyle ou analogue; et R?18¿, R?19¿, R?20¿, R?21¿ et R?22¿ sont chacun, indépendamment, hydrogène, alkyle inférieur éventuellement substitué ou analogue.

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