Liquid-assisted Wittig reaction is used to synthesis of Rosuvastatin intermediates (1,3-Dioxane-4-acetic acid, (4R,6S)-6-[(1E)-2-[4-(4-fluorophenyl)-6- (1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,1-dimethylethyl ester). Evaluate the reaction using common green chemistry metrics: environmental factor (E-factor), and systematic investigation of the reaction has been made in order to study the various factors affecting the reaction. The E-factor of Liquid-assisted Wittig reaction is about a quarter of the traditional method. Under optimal conditions, the conversion rate can reach 99.2 and the E:Z ratio can reach 76:24.
Cite this paper
Yan, J. and Jiang, C. (2020). Mechanochemical Synthesis of Rosuvastatin Intermediates by Liquid-Assisted Wittig Reaction. Open Access Library Journal, 7, e6421. doi: http://dx.doi.org/10.4236/oalib.1106421.
Hoffmann, M., Deshmukh, S. and Werner, T. (2015) Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction. European Journal of Organic Chemistry, 20, 4532-4543. https://doi.org/10.1002/ejoc.201500310
Dogan, S., Duivenvoorden, R., Grobbee, D.E., et al. (2010) Ultrasound Protocols to Measure Carotid Intima-Media Thickness in Trials; Comparison of Reproducibility, Rate of Progression, and Effect of Intervention in Subjects with Familial Hypercholesterolemia and Subjects with Mixed Dyslipidemia. Annals of Medicine, 42, 447-464. https://doi.org/10.3109/07853890.2010.499132
Uchiyama, Y., Ohtsuki, T., Murakami, R., Shibata, M. and Sugimoto, J. (2017) (E)-Selective Wittig Reactions between a Nonstabilized Phosphonium Ylide Bearing a Phosphastibatriptycene Skeleton and Benzaldehydes. European Journal of Organic Chemistry, 2017, 159-174. https://doi.org/10.1002/ejoc.201601098
Valkute, T.R., Aratikatla, E.K. and Bhattacharya, A.K. (2017) Efficient Synthesis of Functionalized Olefins by Wittig Reaction Using Amberlite Resin as a Mild Base. Synthetic Communications, 47, 581-589.
Westman, G., Wennerstr？m, O. and Raston, I. (1993) On the Effect of Cyclodextrin on the Z/E-Selectivity of Wittig Reactions with Semistabilized Ylides. Tetrahedron, 49, 483-488. https://doi.org/10.1016/S0040-4020(01)80315-X
Ward Jr., W.J. and McEwen, W.E. (1990) Metal Ion Effects in Wittig Reactions. A General Hypothesis for the Mechanism of the Wittig Reaction. The Journal of Organic Chemistry, 55, 493-500. https://doi.org/10.1021/jo00289a021
Balema, V.P., Wiench, J.W., Pruski, M. and Pecharsky, V.K. (2002) Mechanically Induced Solid-State Generation of Phosphorus Ylides and the Solvent-Free Wittig Reaction. Journal of the American Chemical Society, 124, 6244-6245.
Ribeiro, M.G.T.C., Costa, D.A. and Machado, A.A.S.C. (2010) “Green Star”: A Holistic Green Chemistry Metric for Evaluation of Teaching Laboratory Experiments. Green Chemistry Letters and Reviews, 3, 149-159.