Triethylamine → Bicyclo(3.2.1)octane-2,4-dione

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Reaction Steps

Analogously to Example P3, 2.76 g (20 mmol) of 4-methylene-3-oxabicyclo[3.2.1]octan-2-one are stirred for 15 hours at room temperature in the presence of 2.23 g (22 mmol) of triethylamine and 0.13 g (2 mmol) of potassium cyanide in 10 ml of acetonitrile. The mixture is heated at 55° for a further 30 minutes and then taken up in water and the neutral components are removed at pH 10 using ethyl acetate. The aqueous phase, acidified to pH 2, is extracted with ethyl acetate, dried over sodium sulfate and concentrated by evaporation, yielding 2.05 g (74.3%0) of pure bicyclo[3.2.1]octane-2,4-dione having a melting point of 129-130° C.

Provenance & Evidence