Patent ID: 8399685

Claim:
A process for producing a thiophene compound or an intermediate of said thiophene compound, the process comprising: (A) reacting a 2-aryl acetate compound represented by formula (1): wherein: R 1 is a C 6-10 aryl group, a C 1-5 heteroaryl group, wherein the C 6-10 aryl group and the C 1-5 heteroaryl group are unsubstituted or substituted with one or more halogen atom, one or more carboxy groups, one or more nitro groups, one or more formyl groups, one or more cyano groups, one or more hydroxy groups, one or more protected hydroxy groups, one or more thiol groups, one or more amino groups, one or more C 1-10 alkyl groups, one or more C 2-6 alkenyl groups, one or more C 2-6 alkynyl groups, one or more C 1-10 alkoxy groups, one or more C 1-10 alkylcarbonyl groups, one or more C 1-10 alkylcarbonyloxy groups, one or more C 1-10 alkoxycarbonyl groups or one or more C 6-10 aryl groups, wherein the C 1-10 alkyl groups, the C 2-6 alkenyl groups, the C 2-6 alkynyl groups, the C 1-10 alkoxy groups, the C 1-10 alkylcarbonyl groups, the C 1-10 alkylcarbonyloxy groups, the C 1-10 alkoxycarbonyl groups and the C 6-10 aryl groups are unsubstituted or substituted with one or more halogen atoms; R 4 is a C 1-3 alkyl group which is unsubstituted or substituted with one or more halogen atoms; and X is a leaving group, with a thioacetic acid compound represented by formula (2): AcSM(2), wherein: Ac is an acetyl group which is unsubstituted or substituted with one or more C 1-3 alkyl groups, which are unsubstituted or substituted with one or more halogen atoms, or one or more halogen atoms; and M is a hydrogen atom or a metal salt, to form a thioacetyl compound represented by formula (3): (B) hydrolyzing the thioacetyl compound; (C) reacting a resulting thiol compound after isolation or without isolation with a vinyl ketone compound represented by a formula (4): wherein each of R 2 and R 3 , independent of each other, are a hydrogen atom, a C 1-6 alkyl group, or a C 6-10 aryl group, wherein the C 1-6 alkyl group and the C 6-10 aryl group are unsubstituted or substituted with one or more halogen atoms, one or more nitro group, one or more cyano groups, one or more hydroxy groups, one or more protected hydroxy groups, one or more thiol groups, one or more amino groups, one or more C 1-10 alkyl groups, one or more C 2-6 alkenyl groups, one or more C 2-6 alkynyl groups, one or more C 1-10 alkoxy groups or one or more C 6-10 aryl groups, wherein the C 1-10 alkyl groups, the C 2-6 alkenyl groups, the C 2-6 alkynyl groups, the C 1-10 alkoxy groups and the C 6-10 aryl group are unsubstituted or substituted with one or more halogen atoms, to form a γ-ketosulfide compound represented by formula (5): (D) cyclizing the γ-ketosulfide compound under basic conditions to form a dihydrothiophene compound represented by formula (6): and (E) oxidizing the dihydrothiophene compound with an oxidizing agent to produce a 2-aryl-3-hydroxy-4-substituted carbonyl thiophene compound represented by formula (7):