H. Bing
2008
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Journal
Chinese Journal of Applied Chemistry
Abstract
2-Formyl-3-acetyl-4-methyl-5-carbobenzoxypyrrole(6) was synthesized via the selective oxidation of 2,4-dimethyl-3-acetyl-5-carbobenzoxypyrrole(5),which was produced from acetylacetic benzylester(1) via nitrosation,reduction and addition-cyclization with acetylacetone.The total yield of the product was about 34%.The effects of reaction conditions and oxidants on the yield of compound 5 and the selective oxidation were studied,respectively.The results show that the yield of compound 5 reached a maximum of 65% under the optimum reaction conditions,where the pH of the reaction medium was 3.8~4.0,the reaction temperature was 85~90 ℃,and the molar ratio of zinc powder to compound 1 was 2.6:1.The optimum oxidant for the selective oxidation of α-methyl on compound 5 was sulfuryl chloride,and the yield of the product was 52.5%.The structures of the compounds were characterized by elemental analysis,1H NMR,IR,and MS spectra.