Diethyl Ether → Methyl 3-(1-naphthyl)-2-oxopropanoate

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Reaction Steps

Sodium (677 mg, 29.4 mmol) is dissolved in ethanol (48 ml). To the solution are added 1-naphthylacetonitrile (5.07 g, 30.3 mmol), then after 20 min. diethyl oxalate (4.1 ml, 30.3 mmol) at r.t. and the mixture is stirred at r.t. for 2 hrs. and refluxed for 1 hour. After cooling to r.t. acetic acid (2 ml) is added. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated in vacuo to give 3-cyano-3-(1-napththyl)pyruvate. A mixture of 3-cyano-3-(1-naphthyl)pyruvate (6.56 g, 24.6 mmol) and 30% sulfric acid (400 ml) is heated at 100° C. for 2 hrs. After cooling, the mixture is extracted with ethyl acetate. The organic layer is dried over magnesium sulfate and evaporated on vacuo to give 3-(1-naphthyl)pyruvic acid. To a solution of 3-(1-naphthyl)pyruvic acid(1.86 g, 8.7 mmol) in diethyl ether (20 ml) is added diazomethane diethyl ether solution (25 ml). The mixture is concentrated in vacuo and the residue is chromatographed on silica gel with hexane and ethyl acetate (3:2) to give methyl 3-(1-naphthyl)pyruvate.

Provenance & Evidence