Citation:
JIAO Li-Juan, LI Ji-Long, DING Dao-Jun, CHEN Ying, ZHANG Mian. Synthesis of A Novel α-Methoxylmethyl Pyrrole[J]. Chinese Journal of Applied Chemistry,
;2010, 27(1): 48-52.
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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.
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Keywords:
- Knorr condensation,
- pyrrole,
- synthesis
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