摘要
以乙酰乙酸乙酯(1)为原料,以醋酸为反应介质,通过与亚硝酸钠的肟化反应得到化合物N-羟基亚胺乙酰乙酸乙酯(2),化合物2在缓冲的乙酸溶液中通过锌粉还原、与环己酮(3)加成环化反应生成化合物2-乙氧羰基-3-甲基-4,5-四亚甲基吡咯(4),反应的总收率为38.95%.而采用"一锅煮"合成方法制备化合物4可使反应的总收率达到49.76%.考察了在该反应体系的pH值为3.8～4.0时,其他一些反应条件对目标化合物4合成收率的影响,确定了最佳的反应条件为:锌粉与反应物1的摩尔比为2.9:1,反应温度为95～100℃.所合成的化合物的结构用元素分析、IR、1HNMR等测试手段进行了表征.
N-hydroxyimino ethyl acetoacetate（2） was prepared from ethyl acetoacetate（1） and NaNO2 via oximination using acetic acid instead of vitriol as reaction medium,and compound 2 was reacted with cyclohexanone（3） by means of reduction of zinc dust and addition-cyclization in buffered acetic acid solvent to give 2-ethoxycarbonyl-3-methyl-4,5-tetramethylenepyrrole（4） with an about 38.95% overall yield.However,the total yield of compound 4 prepared by ＂one-pot＂ method reached a maximum of 49.76%.The effects of some other reaction conditions on the yield of object compound 4 were examined when the pH of the above mentioned reaction system is in the range of from 3.8 to 4.0,and the optimum reaction conditions were determined as follows：the molar ratio of zinc powder to compound（1） was 2.9：1 and the reaction temperature is set as 95～100 ℃.The structures of the obtained compounds were characterized by elemental analysis,IR,1HNMR,et al.
出处
《江西师范大学学报（自然科学版）》
CAS
北大核心
2010年第3期227-231,共5页
Journal of Jiangxi Normal University(Natural Science Edition)
基金
河南省科技厅科技攻关项目(082102210050)
河南省教育厅自然科学研究计划(2008B150018)资助项目
