Modified Synthesis of 2-Ethoxycarbonyl-3,4-Diethyl-Pyrrole and the Corresponding Octaethylporphyrin

Qi Feng Liu

doi:10.4028/www.scientific.net/AMR.884-885.465

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HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 884-885Modified Synthesis of...

Modified Synthesis of 2-Ethoxycarbonyl-3,4-Diethyl-Pyrrole and the Corresponding Octaethylporphyrin

Abstract:

In the synthesis of 2-ethoxycarbonyl-3, 4-diethyl-pyrrole (1) by the Barton-Zard reaction of 4-acetoxy-3-nitrohexane (1b) with ethyl isocyanoacetate, the organic base 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) and the solvent tetrahydrofuran (THF) were replaced with K₂CO₃ and ethanol, respectively. Moreover, the preparation of the intermediate 1b from 1a by acetylation reaction was carried out by employing acetyl chloride in boiling toluene solution instead of acetic anhydride and the catalyst concentrated sulfuric acid. After treatment of 1 with excess LiAlH₄ at low temperature, the crude product 1c (α-hydroxymethyl-3, 4-diethyl-pyrrole) was immediately reacted via a tetramerization in the presence of the catalyst BF₃.OEt₂ in crude CHCl₃,followed by oxidation of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) to provide the corresponding octaethylporphyrin 2. The results indicate that using BF₃.OEt₂ as catalyst instead of p-toluenesulphonic acid (p-TsOH)in the synthesis of 2 from 1c can obviously increase the yield of product 2 up to 80% from 69%.