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Synthesis of coumarin derivatives in a microfluidic flow system employing the Pechmann condensation: A case study
Journal of the Chinese Chemical Society ( IF 1.6 ) Pub Date : 2020-11-13 , DOI: 10.1002/jccs.202000371
Ling‐Kang Liu, Jhao‐Hong Deng, Yang‐Ming Guo

For the synthesis of coumarin derivatives using the Pechmann condensation scheme, an acidic ionic liquid catalyst, abbreviated as [EBsImH][HSO4], was prepared from the ring opening of 1,4‐butanesultone by 1‐ethylimidazole, followed by the addition of 1 equiv. H2SO4(c). The [EBsImH][HSO4]‐catalyzed Pechmann condensation reactions proceeded smoothly in a batch setup, with recyclable [EBsImH][HSO4] showing great catalytic activity. The acidic ionic liquid catalyst [EBsImH][HSO4] was recovered from EtOAc/H2O extraction of the product mixture, where the H2O layer was worked up and dried for reuse in consecutive runs of the Pechmann condensation reactions, maintaining >85% conversion for four times. The catalytic reactions were also carried out in a microfluidic flow setup. The flow parameters, the reactant molar amounts, and the additional H2SO4 as a modifying acid catalyst were optimized in the current case study. A minimum conversion rate of 2.8 g/hr of coumarin derivatives was demonstrated.

中文翻译:

Pechmann缩合反应在微流系统中香豆素衍生物的合成:案例研究

为了使用Pechmann缩合方案合成香豆素衍生物,从1,4-丁磺酸内酯与1-乙基咪唑的开环反应中制备了一种酸性离子液体催化剂,缩写为[EBsImH] [HSO 4 ]。 1当量 H 2 SO 4c)。的[EBsImH] [HSO 4 ] -催化的在间歇设置顺利pechmann缩合反应的反应,使用可回收[EBsImH] [HSO 4 ]表现出极大的催化活性。从EtOAc / H 2中回收酸性离子液体催化剂[EBsImH] [HSO 4 ]O萃取产物混合物,在其中处理H 2 O层并干燥以在Pechmann缩合反应的连续运行中重复使用,保持> 85%的转化率四次。催化反应也以微流体流动装置进行。在当前案例研究中,优化了流量参数,反应物摩尔量以及作为改性酸催化剂的附加H 2 SO 4。香豆素衍生物的最低转化率为2.8克/小时。
更新日期:2021-01-12
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