Dimethylformamide → 3,5-Dioxohexanoic acid

Participants

Reaction Steps

The iodide 2 (286.6 mg) and 6-hydroxy-α-methylnaphthaleneacetic acid methyl ester (154.0 mg) were dissolved in dimethylformamide (3 ml) and potassium carbonate (277,6 mg) was added. The reaction was stirred at room temperature for 12 hours, after which it was partitioned between water (10 ml) 15 and ethyl acetate (50 ml). The layers were separated and the organics were washed with water (3×10 ml) and brine (10 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness. Purification of the residue on silica gel (25% ethyl acetate/hexane) gave the desired triacetate (225.8 mg, 64% yield).

Provenance & Evidence