Ketones from esters

Related Methods Section 117 (Esters from Ketones)... 

The synthesis of -hydroxy acids via their esters from ketones and the Reformatsky reagent is still one of the best approaches for this class of compounds. This reagent. 

Acylation A useful method for preparing 1,3-diketones and -keto esters from ketones is to first form the enamine and then acylate it with an appropriate acyl chloride derivative. Morpholine, a 5ec-amine, is a good choice for this purpose since the derived enamines have lower reactivity toward acyl halides, allowing for more control of the reaction. 

Baeyer-Villiger oxidation Formation of esters from ketones upon peracid oxidation. 28... 

Quite apart from the Issue of regioselectivlty, the present method is exceptionally reliable and makes It possible to prepare 3-keto esters from ketones under especially mild conditions. It is not only the method of choice with sensitive substrates, but will often ensure superior results with more stable intermediates as well.B iB A wide range of examples Is provided in the Table, while further examples have been reported elsewhere.The methodology has also been applied to... 

Reaction with ketones (1, 369-370). Mock and Hartman3 have improved the original procedure for synthesis of /3-keto esters from ketones by using triethyl-oxonium fluoroborate as the Lewis acid catalyst rather than boron trifluoride. Thus cyclohexanone (1) is converted into 2-carboethoxycycloheptanone (2) in 90% yield under the new conditions the yield using BF3 was 38%. The reaction is... 

Ketocarboxylic acid esters from ketones H —>- COOR... 

Darzens-Claiscn reaction Glycidic acid esters from ketones and a-halogenocarboxylic acid esters... 

Peroxyphthalic acid Baeyer-Villiger oxidation Carboxylic acid esters from ketones... 

Reactions of Reformatskii products a,/ - thylenecarboxylic acid esters from ketones via / -acetoxycarboxylic acid esters Bicyclo[2.2.2]octene ring fragmentation... 

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