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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. shu

Synthesis of A Novel α-Methoxylmethyl Pyrrole

1.
College of Chemistry and Material Science, Anhui Normal University, Wuhu 241000

Received Date: 8 January 2009
Available Online: 25 April 2009
Fund Project: 国家自然科学基金(20802002) (20802002)安徽省教育厅基金(KJ2009A130) 资助项目 (KJ2009A130)

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.
- Knorr condensation,
- pyrrole,
- synthesis
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