Clauson-Kaas吡咯合成反应

2,5-二烷氧基四氢呋喃和伯胺反应制备N-取代吡咯的反应。此反应是一种保护伯胺的方法。此方法得到的吡咯，官能团耐受度高，可以进行各种高活性的反应。

1-(2-Methoxycarbonyl)phenylpyrrole (3). 2,5-Diethoxytetrahydrofuran 1 (95.5 g, 0.59 mol) was added to a well stirred solution of methyl anthranilate 2 (90 g, 0.59 mol) in AcOH (265 mL). During the exothermic reaction, the mixture became clear deep red. The mixture was heated to reflux for 1 h and the solvent was removed in vacuo. Fractional distillation in vacuo gave 95.8 g of 3 (80%), bp 90–95 C.

【Josey AD, J Org Chem., 1962, 27, 2466】

相关文献

1 Clauson-Kaas N Acta Chem Scand 1952 6 667

2 Josey AD J Org Chem 1962 27 2466

3 Patterson JM Synthesis 1976 281

4 Lellouche J-P Tet Lett 2000 41 3725

5 Zaban A, Lellouche JP J Org Chem 2006 71 9139

6 Smith JA Tet Lett 2006 47 799

7 Aaron JJ ARKIVOC 2008 xvii 122

8 Ketcha DM ARKIVOC 2009 xiv 181

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 196.