Ethyl 2-acetyl-5-oxohexanoate

Henecka,71 for instance obtained ethyl 2-acetyl-5-oxohexanoate from ethyl acetoacetate and methyl vinyl ketone as follows ... 

Using your roadmaps as a guide, show how to convert ethanol, formaldehyde, and acetone into racemic ethyl 2-acetyl-5-oxohexanoate.You must use ethanol, formaldehyde, and acetone as the source of aU carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. 

Ethyl 2-acetyl-5-oxohexanoate refluxed 1 hr. with pyrrolidine and acetic acid in 9 1 methanol-water -> ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate. Y 84%. F. e. and formation of isomers under different conditions s. A. L. Begbie and B.T. Golding, Soc. Perkin I 1972, 602. 

In the same area, an asymmetric domino double Michael reaction was initiated by this catalyst, providing an expedited access to chiral multi-functionalised live-membered rings. This time, the reaction occurred between a nitroalkene and ethyl 2-acetyl-5-oxohexanoate, yielding the desired double Michael adducts in high yields and excellent diastereo- and enantio-selectivities (Scheme 1.66). An immense potential of synthetic versatility of the... 

Much more studied is the reaction of /8-dicarbonyl compounds with 2-amino-2-deoxyaldoses in particular, with 2-amino-2-deoxy-D-glu-cose (55), both in neutral and alkaline medium. In neutral methanol or aqueous acetone, 2-amino-2-deoxy-D-glucose reacts with 2,4-pen-tanedione to give52 54 3-acetyl-2-methyl-5-(D-arabino-tetrahydroxy-butyl)pyrrole (56a), and, with ethyl acetoacetate,55 the pyrrole 56b. Similar (tetrahydroxybutyl)pyrroles have been prepared from other /3-keto esters, such as ethyl 3-oxohexanoate, ethyl thiolacetoacetate, and diethyl 3-oxopentanedioate.53,56,56a... 

Ethyl (/ )-2-Acetyl-2-methyl-5-oxohexanoate Typical Procedure235 ... 

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