Pyridine N-Oxide → Methyl 3,3-dimethyl-5-oxovalerate

Participants

Reaction Steps

A mixture of methyl 5-bromo-3,3-dimethylpentanoate (5.0 g), pyridine-N-oxide (4.49 g), sodium bicarbonate (3.77 g) and toluene (30 cm3) was heated at the reflux temperature with vigorous agitation for a period of 14 hours. After cooling the mixture to the ambient temperature, water (20 cm3), saturated ammonium carbonate solution (20 cm3) and toluene (50 cm3) were added and the aqueous phase separated and extracted with toluene (3×75 cm3). The toluene extracts were added to the main organic phase and the whole dried over anhydrous magnesium sulphate concentrated by evaporation of the more volatile components under reduced pressure. The residual liquid was purified by Kugelrohr distillation (130° C./water pump pressure) to give methyl 3,3-dimethyl-5-oxopentanoate in 63% yield.

Provenance & Evidence