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Practical Large Scale Synthesis of Half-Esters of Malonic Acid 원문보기

Chemical & pharmaceutical bulletin, v.57 no.5, 2009년, pp.508 - 510  

Niwayama, Satomi (Department of Chemistry and Biochemistry, Texas Tech University) ,  Cho, Hanjoung (Department of Chemistry and Biochemistry, Texas Tech University)

Abstract AI-Helper 아이콘AI-Helper

A practical large-scale synthesis of monomethyl malonate and monoethyl malonate, which are among the most commonly applied half-esters in organic synthesis, is described, applying the highly efficient selective monohydrolysis of symmetric diesters we reported before. The optimal conditions with rega...

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참고문헌 (28)

  1. 1) This work is the subject of U.S. and international patent applications. Niwayama S., U.S. 2009/0023945, WO 2008/150487. 

  2. Bulychev, Alexey, Bellettini, John R., O'Brien, Michael, Crocker, Peter J., Samama, Jean-Pierre, Miller, Marvin J., Mobashery, Shahriar. N-Sulfonyloxy-β-lactam Inhibitors for β-Lactamases. Tetrahedron, vol.56, no.31, 5719-5728.

  3. Bihovsky, Ron, Pendrak, Israil. Synthesis of cystamidin a (pyrrole-3-propanamide), a reported calpain inhibitor. Bioorganic & medicinal chemistry letters, vol.6, no.13, 1541-1542.

  4. 10.1055/s-1996-5333 

  5. Keum, G., Hwang, C. H., Kang, S. B., Kim, Y., Lee, E.. Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin. Journal of the American Chemical Society, vol.127, no.29, 10396-10399.

  6. Kim, H.-J., Lindsey, J. S.. De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles: Bacteriochlorins and a Tetradehydrocorrin. Journal of organic chemistry, vol.70, no.14, 5475-5486.

  7. Knölker, Hans-Joachim, Wolpert, Marcus. Transition metal complexes in organic synthesis, part 36. Cyclization of tricarbonyliron complexes by oxygen to 4a,9a-dihydro-9H-carbazoles: Application to the synthesis of mukonine, mukonidine, and pyrido[3,2,1-jk]carbazoles. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.38, no.4, 533-536.

  8. Marcaccini, S., Pepino, R., Pozo, M., Basurto, S., Garci@?a-Valverde, M., Torroba, T.. One-pot synthesis of quinolin-2-(1H)-ones via tandem Ugi-Knoevenagel condensations. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.45, no.21, 3999-4001.

  9. List, Benjamin, Doehring, Arno, Hechavarria Fonseca, Maria T., Job, Andreas, Rios Torres, Ramon. A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-α,β-unsaturated esters from aldehydes. Tetrahedron, vol.62, no.2, 476-482.

  10. Balasubramanian, Thiagarajan, Lindsey, Jonathan S.. Synthesis of β-substituted porphyrin building blocks and conversion to diphenylethyne-linked porphyrin dimers. Tetrahedron, vol.55, no.22, 6771-6784.

  11. Hudson, R. D. A., Osborne, S. A., Stephenson, G. R.. Reactions of a New Sorensen-type Nucleophile with Organoiron Complexes: Synthesis of N-Deprotected, Diastereomerically Pure Amino Acids. Synlett : accounts and rapid communications in synthetic organic chemistry, vol.1996, no.9, 845-.

  12. 0385-5414 Heterocycles Ashton M. J., Hills S. J., Newton C 28 1014 1989 

  13. 0385-5414 Heterocycles WILLIAMS DAVID R. 67 2 555 2006 10.3987/COM-05-S(T)70 

  14. 0078-6209 Organic Syntheses Strube R. E. 4 417 1963 

  15. 0078-6209 Organic Syntheses Hutchinson C. R., Nakane M., Gollma 7 323 1990 

  16. Grakauskas, Vytautas, Guest, Allen M.. Dinitromethane. Journal of organic chemistry, vol.43, no.18, 3485-3488.

  17. Rigo, B., Fasseur, D., Cauliez, P., Couturier, D.. Reaction of trimethylsilyl derivatives with Meldrum's acid : A new and easy monofunctionalization of malonic acid. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.30, no.23, 3073-3076.

  18. Synthesis Junek H., Ziegler E., Herzog U., Kr 1976 332 1976 10.1055/s-1976-24041 

  19. Ozaki, Eiji, Uragaki, Toshitaka, Sakashita, Keiichi, Sakimae, Akihiro. Enzymatic Preparation of Alkanedicarboxylic Acid Monoesters. Chemistry letters, vol.24, no.7, 539-540.

  20. 0040-4039 Tetrahedron Lett. Krapcho A. P., Jahngen E. G. E. Jr. 15 2721 1974 10.1016/S0040-4039(01)91723-X 

  21. Niwayama, S.. Highly Efficient Selective Monohydrolysis of Symmetric Diesters. Journal of organic chemistry, vol.65, no.18, 5834-5836.

  22. Niwayama, S., Cho, H., Lin, C.. Highly efficient selective monohydrolysis of dialkyl malonates and their derivatives. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.49, no.28, 4434-4436.

  23. Niwayama, S., Wang, H., Hiraga, Y., Clayton, J.C.. Influence of co-solvents in the highly efficient selective monohydrolysis of a symmetric diester. Tetrahedron letters: the international organ for the rapid publication of preliminary communications in organic chemistry, vol.48, no.48, 8508-8510.

  24. Niwayama, Satomi, Rimkus, Audrius. Effects of Counter Cations in Selective Monohydrolyses of Symmetric Diesters. Bulletin of the Chemical Society of Japan, vol.78, no.3, 498-500.

  25. 0037-9980 J. Synth. Org. Chem., Jpn. NIWAYAMA SATOMI 66 10 983 2008 10.5059/yukigoseikyokaishi.66.983 

  26. 26) Under comparable conditions on a 0.12 mol-scale with a reaction time of 1 h, we have also obtained the half-esters of dimethyl methyl malonate and diethyl methyl malonate in 90% and 83% yields, respectively. 

  27. 27) Under the same pressure, 6.55 g (4%) of dimethyl malonate was collected at 45 °C, and 1.31 g (1%) of malonic acid remained after the distillation. 

  28. 28) Under the same pressure, 5.60 g (4%) of diethyl malonate was collected at 43 °C, and 4.79 g (6%) of malonic acid remained after the distillation. 

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