Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → HCID 19800636, compound

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Reaction Steps

A stirred mixture of nitro-2-propanone (63.50 g, 0.616 mol), (ethoxymethylene)oxalacetic acid, diethyl ester (151.1 g, 0.616 mol) and ethanol at 5° C. under a nitrogen atmosphere is treated with sodium acetate (101.1 g, 1.23 mol), stirred overnight at room temperature, and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 1% ethyl acetate:hexanes eluent). The chromatographed material is taken up in ethyl acetate and extracted with an equivalent of aqueous sodium hydroxide. The basic layer is acidified to pH 2-3 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract is dried and concentrated in vacuo to give the title product as a yellow oil, 16.0 g, identified by NMR and mass spectral analyses.

Provenance & Evidence