Methyl 2-oxoacetate

Uses

Methyl Glyoxylate is a useful compound for preparation of pyridine and quinoline derivatives.

Preparation

Preparative Methods of Methyl 2-oxoacetate: efficient methods include oxidative cleavage of tartrate diesters, ozonolysis of maleate/fumarate derivatives, exchange reaction between appropriate dialkoxyacetate and glyoxylic acid, and NaOAc-catalyzed elimination of nitrite ion from nitrate esters.^[1]

General Description

Methyl Glyoxylate is a two-carbon synthon utilized in electrocyclic processes (Diels-Alder reaction, ene reactions), various condensations (Mannich, aldol, Wittig, Prins, acyloin), carbinolamine formation, and Friedel-Crafts reactions.

storage

Methyl 2-oxoacetate stores under N2 in a refrigerator due to their tendency to form a monohydrate and/or polymerize.

References

1. (a) Wolf, F. J.; Weijland, J. OSC 1963, 4, 124. (b) Jung, M. E.; Shishido, K.; Davis, L. H. JOC 1982, 47, 891. (c) Blake, J.; Tretter, J. R.; Juhasz, G. J.; Bonthrone, W.; Rappoport, H. JACS 1966, 88, 4061. (d) Haggerty, J. G.; Kelly, T. R.; Schmidt, T. E. S 1972, 544. Hook, J. M. SC 1984, 14, 83. (e) Kornblum, N.; Frazier, H. W. JACS 1966, 88, 865.