Process for producing thiophene compound and intermediate...

C - Chemistry – Metallurgy – 07 – D

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C07D 333/32 (2006.01) C07C 319/18 (2006.01) C07C 323/56 (2006.01) C07C 327/32 (2006.01)

Patent

CA 2717065

To provide a novel process for producing a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound or an intermediate thereof useful as an intermediate for production of medicines and agricultural chemicals. A 2-aryl acetate compound represented by the formula (1): Image wherein R' is an aryl group or the like, R4 is a C1-3 alkyl group or the like, and X is a leaving group, is reacted with a thioacetic acid compound to form a thioacetyl compound (3), the thioacetyl compound (3) is reacted with a vinyl ketone compound to form a .gamma.-ketosulfide compound (5), which is cyclized under basic conditions to form a dihydrothiophene compound (6), and the dihydrothiophene compound (6) is oxidized by using an oxidizing agent to produce a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound (7).

L'invention concerne un nouveau procédé pour produire un composé 2-aryl-3-hydroxy-4-substituant-carbonylthiophène, qui est un composé utile comme intermédiaire pour la production d'un agent pharmaceutique ou d'un agent pour l'agriculture, ou un intermédiaire pour la production du composé 2-aryl-3-hydroxy-4-substituant-carbonylthiophène. Un composé 2-aryl-3-hydroxy-4-substituant-carbonylthiophène (7) peut être produit par : réaction d'un composé ester d'acide 2-arylacétique représenté par la formule (1) [dans laquelle R1 représente un groupe aryle ou similaire ; R4 représente un groupe alkyle en C1-3 ou similaire ; et X représente un groupe libérable] avec un composé acide thioacétique pour produire un composé thioacétyle (3) ; réaction du composé thioacétyle (3) avec un composé vinylcétone pour produire un composé ?-cétosulfure (5) ; cyclisation du composé ?-cétosulfure (5) dans des conditions basiques pour produire un composé dihydrothiophène (6) ; oxydation du composé dihydrothiophène (6) avec un agent oxydant pour produire le composé 2-aryl-3-hydroxy-4-substituant-carbonylthiophène (7). (1) (3) (5) (7) (7)

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