Diethyl Ether → 3-(Dimethylamino)-2,2-dimethylpropyl 3-oxobutanoate

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Reaction Conditions

Reaction Steps

To a solution of 1.71 g of 3-(N,N-dimethylamino-2,2-dimethylpropanol (Reference: M. S. Newman et al; Journal of Medicinal chemistry, vol 15, p1003 (1972)) in 2 ml of benzene was added dropwise 1.16 g of diketene with stirring at 70° C. The mixture was stirred at 70° C. for additional 1.5 hr. Solvent was distilled off in cacuo to leave a yellowish oil. The residue was dissolved in diethyl ether and then extracted with an aqueous 2N-hydrochloric acid solution. The extracts were made alkaline with an aqueous 2N sodium hydroxide solution. The mixture was extracted with diethyl ether and then the ethereal extract was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off to give 2.8 g of 3-(N,N-dimethylamino)-2,2-dimethylpropyl acetoacetate can oily substance. The physical properties of this compound are as follows.

Provenance & Evidence