Blaise reaction
From Wikipedia, the free encyclopedia
The Blaise reaction is an organic reaction that forms a β-ketoester from the reaction of zinc metal with a α-bromoester and a nitrile. The final intermediate is a metaloimine, which is hydrolyzed to give the desired β-ketoester.
Bulky aliphatic esters tend to give higher yields. Hannick and Kishi have developed an improved procedure.
It has been noted that free hydroxyl groups can be tolerated in the course of this reaction, which is surprising for reactions of organometal halides.
[edit] References
- ^ Blaise, E. E.; Compt. Rend. 1901, 132, 478.
- ^ Rinehart, K. L., Jr. Organic Syntheses, Coll. Vol. 4, p.120 (1963); Vol. 35, p.15 (1955). (Article)
- ^ Cason, J.; Rinehart, K. L., Jr.; Thorston, S. D., Jr. J. Org. Chem. 1953, 18, 1594. (DOI:10.1021/jo50017a022)
- ^ Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833. (DOI:10.1021/jo00169a053)
- Marko, I.E. J. Am. Chem. Soc. 2007, ASAP DOI:10.1021/ja0691728
- Wang, D.; Yue, J.-M. Synlett 2005, 2077-2079.
