Blaise reaction
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. Steven Hannick and Yoshito 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.
Organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
that forms a β-ketoester from the reaction of zinc
Zinc
Zinc , or spelter , is a metallic chemical element; it has the symbol Zn and atomic number 30. It is the first element in group 12 of the periodic table. Zinc is, in some respects, chemically similar to magnesium, because its ion is of similar size and its only common oxidation state is +2...
metal with a α-bromoester
Haloketone
A haloketone in organic chemistry is a functional group consisting of a ketone group or more general a carbonyl group with a α-halogen substituent. The general structure is RR'CCR where R is an alkyl or aryl residue and X any one of the halogens...
and a nitrile
Nitrile
A nitrile is any organic compound that has a -C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, one example being super glue .Inorganic compounds containing the -C≡N group are not called...
. The final intermediate is a metaloimine, which is hydrolyzed to give the desired β-ketoester.
Bulky aliphatic esters tend to give higher yields. Steven Hannick and Yoshito Kishi
Yoshito Kishi
Yoshito Kishi is the Morris Loeb Professor of Chemistry at Harvard University. He is known for his contributions to the sciences of organic synthesis and total synthesis....
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.