Potassium carbonate as a base for cycloalkylation of diethyl malonate and ethyl cyanoacetate in solid-liquid two phase systems

Subject Areas : Journal of the Iranian Chemical Research

Fuping Liu ¹ ( School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, China )
Yan Zhu ² ( School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, China )
Ming Lu ³ ( School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, China )

Received: 2008-06-04 Accepted : 2008-09-14 Published : 2008-11-20

Keywords: Diethyl malonate, Ethyl cyanoacetate, Potassium carbonate, Phase transfer catalyst, Toluene,

Abstract :

The cycloalkylation of diethyl malonate and ethyl cyanoacetate with alkyl dihalide was investigated by using comminuted potassium carbonate as a base and toluene as a solvent in the presence of hexadecyltrimethylammonium bromide (HTMAB) as a phase-transfer catalyst, which provided a conventional procedure with the advantage of short reaction period and high product yield. The factors influencing the product yield and the reaction mechanism were discussed on the basis of the experimental data.

References:

[1] W. Dmowski, A. Wolniewicz, J. Fluorine. Chem. 102 (2000) 141.
[2] S.Y. Nishino, EP Patent 1, 671, 937, 2006.
[3] B. Torok, A. Molnar, J. Chem. Soc., Perkin. Trans 1 (1993) 801.
[4] C.Y. Zhou, D.M. Chen, Y.Z. Jiang, Synth. Common. 17 (1987) 1377.
[5] S.M. Ma, S.H. Yin, L.T. Li, F.G. Tao, Org. Lett. 4 (2002) 505.
[6] D. Albanese, D. Landini, M.J. Penso, Org. Chem. 57 (1992) 1603.
[7] Y.R. Jorapur, J.M. Jeong, D.Y. Chi, Tetra. Lett. 47 (2006) 2435.
[8] A.T. Ben, B.Y. Le, G.R. El, M. Delmas, A.Gaset, Synth. Common. 22 (1992) 1421.
[9] M.Z. Jászay, I. Petneházy, L. Töke, B. Szajáni, Synthesis (1987) 520.
[10] W.J. Balley, J.J. Daly, J. Am. Chem. Soc. 81 (1959) 5397.
[11] R.H. Harnest, A. Burger, J. Am. Chem. Soc. 65 (1943) 370.
[12] H.R. Henze, R.L. Mckee, J. Am. Chem. Soc. 64 (1942) 1672.
[13] C. Galli, G. Illuminati, L. Mandolini, P. Tamborra, J. Am. Chem. Soc. 99 (1977) 2591.
[14] D.F. Detar, N.P. Luthra, J. Am. Chem. Soc. 102 (1980) 4505.
[15] A.D. Cort, L. Mandolini, B. Masci, J. Org. Chem. 48 (1983) 3979.
[16] H.O. Chang, J.S. Kim, H.H. Jung, J. Org. Chem. 64 (1999) 1338.