Title: Synthesis of A Novel α-Methoxylmethyl Pyrrole
Abstract:2,4-Dimethyl-3-(3-methoxy-3-oxopropyl)-5-benzylcarboxylate-1H-pyrrole(2) and 2,4-dimethyl-3-methoxymethyl-5-benzylcarboxylate-1H-pyrrole(3) were synthesized from benzyl ethylacetate(4) via the Knorr c...2,4-Dimethyl-3-(3-methoxy-3-oxopropyl)-5-benzylcarboxylate-1H-pyrrole(2) and 2,4-dimethyl-3-methoxymethyl-5-benzylcarboxylate-1H-pyrrole(3) were synthesized from benzyl ethylacetate(4) via the Knorr condensation reaction.In the ether solution of bromine,pyrrole(2) was converted to the corresponding dipyrromethane(7) through self-condensation,while no reaction happened to pyrrole(3).Under the 2 mol/L Pb(OAC)4 oxidative condition,when it was twice the concentration of pyrrole(3),at 80 ℃,pyrrole(3) was completely consumed.After the subsequent refluxing in the methanol solution of hydrochloride acid,a novel 2-methoxymethyl-3-methylcarboxylate-4-methyl-5-benzylcarboxylate-1H-pyrrole(1) was synthesized in a yield of 82%.Pyrrole(1),pyrrole(2),pyrrole(3) and dipyrrolemethane(7) were characterized through NMR,elemental analysis,MS and IR.The construction of pyrrole(1) will be helpful for the further study of the structure-functionality relationship of pyrrole derivatives.Read More
Publication Year: 2010
Publication Date: 2010-01-01
Language: en
Type: article
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