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초록· 키워드
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A new synthetic method for tiaprofenic acid, which is a potent anti-inflammatory agent, was described. Friedel-Crafts reaction of thiophene with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)$ acetate (1) gave ethyl ${\alpha}-methylthio-2-thiopheneacetate$ (3). Ethyl ${\alpha}-methyl-2-thiopheneacetate$ (5) was prepared by treatment of (3) with NaH and MeI, followed by desulfurization with zinc dust-acetic acid of the resultant ethyl ${\alpha}-methyl-{\alpha}-methylthio-2-thiopheneacetate$ (4). Tiaprofenic acid (7) could be easily synthesized by benzoylation of (5) and hydrolysis of the resultant ethyl $5-benzoyl-{\alpha}-methyl-2-thiopheneacetate$ (6).
#Tiaprofenic acid
#anti-inflammatory agent
#Friedel-Crafts reaction
#thiphene
#ethyl ${alpha}-chlocro-{alpha}-
#methylthio)$ acetate
#ethyl ${alpha}-methylthio-2-thiopheneacetate$
#ethyl ${alpha}-methyl-2-thiopheneacetate$
#desulfurization
#zinc dust-acetic acid
#ethyl ${alpha}-methyl-{alpha}-methylthio-2-thiopheneacetate$
#benzoylation
#hydrolysis
#ethyl $5-benzoyl-{alpha}-methyl-2-thiopheneacetate$
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