Activation of Zinc By Trimethylchlorosilane: An Improved Procedure For The Preparation of β-hydroxy Esters From Ethyl Bromoacetate And Aldehydes Or Ketones (reformatsky Reaction)

Journal of Organic Chemistry

Volumn 52, Issue 21, 1987, Pages 4796-4798

  Picotin, Gérard ^a   Miginiac, Philippe ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281940     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00230a029     Document Type: Article

References (22)

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2. Rathke, M. W. Org. React. (N. Y.) 1975, 22, 423.
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4. Henecka, H. In Methoden der Organischen Chemie, 4th ed.; Muller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1952; Vol. VIII, p 511.
5. Niitzel, K. In Methoden der Organischen Chemie, 4th ed.; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1973, Vol. XIII/2a, p 809.
6. Use of a trimethyl borate-tetrahydrofuran mixture as solvent: Rathke, M. W. J. Org. Chem. 1970, 35, 3966.
7. Use of a zinc-copper couple: Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
8. Use of acid-washed zinc: Frankenfeld, J. W.; Werner, J. J. J. Org. Chem. 1969, 34, 3689.
9. Use of highly activated zinc: Rieke, R. D.; Uhm, S. J. Synthesis 1975,452. Csuk, R.; Furstner, A.; Weidman, H. J. Chem. Soc., Chem. Commun. 1986, 775. Boldrini, G. P.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1983,48, 4108. Rieke, R. D.; Tzu-Jung Li, P.; Burns, T. P.; Uhm, S. T. J. Org. Chem. 1981, 46, 4323
10. Use of a continuous-flow apparatus: Ruppert, J. F.; White, J. D. J. Org. Chem. 1974, 39, 269.
11. Sonic acceleration in 1,4-dioxane: Boudjouk, P.; Han, B. H. J. Org. Chem. 1982, 47, 5030.
12. A similar activation was used to carry out a Reformatsky reaction between ethyl 2-bromopropionate and ethyl formate: Gawronsky, J. K. Tetrahedron Lett. 1984, 25, 2605.
13. (13)This rather unusual order of mixing the reagents is not without precedent: Stoll, M. Helo. Chim. Acta 1951, 34, 678. Klemm, L. H.; Bower, G. M. J. Org. Chem. 1958,23, 344. Inhoffen,. H.; Raspe, G. Justus Liebigs Ann. Chem. 1953,592, 214. Inhoffen,. H. Justus Liebigs Ann. Chem. 1950, 568, 47.
14. The preparation of the zinc bromo ester in an initial step of the Reformatsky reaction has already been described. In diethyl ether: Siegel, A.; Keckeis, H. Monatsh. Chem. 1953,84, 910; Chem. Abstr. 1954, 48, 10545. Vinograd, L. K.; Vulfson, N. S. Dokl. Akad. Nauk SSSR 1958,123, 97; Chem. Abstr. 1959, 53, 5179. Gaudemar, M. Tetrahedron Lett. 1983,24, 2749. In an ether-benzene mixture: Grob, C. A.; Brenneisen, P. Helo. Chim. Acta 1958, 41, 1184. Vaugham, W. R.; Bernstein, S. C.; Lorber,. E. J. Org. Chem. 1965, 30, 1790. In dimethoxymethane: Gaudemar, M.; Cure, J. C. R. Acad. Sci. Paris, Ser. C. 1966, 262, 213. Cure, J.; Gaudemar, M. Bull. Soc. Chim. Fr. 1968, 3244. Gaudemar-Bardone, F.; Gaudemar, M. Bull. Soc. Chim. Fr. 1969, 2088. Cure, J.; Gaudemar, M. Bull. Soc. Chim. Fr. 1969, 2471.
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19. Kuwajima, I.; Nakamura, E.; Hashimoto, K. Org. Synth. 1983, 61, 122.
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22. Note added in proof: for a review dealing with use of activation methods for organozinc reagents, see: Erdik, E. Tetrahedron 1987, 43, 2203.