Diethyl Oxalate → 2-Ethoxalylacenaphthen-1-one

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Reaction Steps

Acenaphthen-1-one (JACS, 62, 432, 1940) (4.1 g) is reacted with diethyl oxalate (4.2 g) in anhydrous ethanol (280 ml) containing sodium ethoxide (from 0.66 g of sodium) at room temperature for 2 hours. The precipitate is filtered and washed with hexane, then is dissolved in water. The aqueous solution is acidified to pH 4 with citric acid and the precipitate is filtered and washed with water. Crystallization from chloroform-hexane gives 2-ethoxalylacenaphthen-1-one, m.p. 101°-103° C. (5.1 g), which is reacted with methylhydrazide (1.3 g) in acetic acid (110 ml) at 60° C. for 4 hours. After cooling the reaction mixture is diluted with ice water and extracted with ethyl acetate.

Provenance & Evidence