Water → 3,3-Bis(ethoxycarbonyl)bicyclo[3.2.0]heptane

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Reaction Steps

In a 250 ml round-bottomed flask equipped with mechanical stirring, reflux condenser, addition funnel and argon inlet was placed 20.2 g of XXI, 12.4 ml diethylmalonate, and 72 ml of dry t-butanol. The reaction mixture was refluxed and a solution of 19.9 g of potassium-t-butoxide in 123 ml of t-butanol was added over 6 hours. The reaction mixture was refluxed for 15 hours. The resulting reaction mixture was cooled by external application of an ice-water bath and an equal volume of water added. The mixture was extracted with ether. The ether extracts were washed with 3 N hydrochloric acid and 5% aqueous sodium bicarbonate, then dried (MgSO4), filtered and distilled in vacuo to yield 10.3 g of the compound XXII as a clear oil: bp 100°-105° C. (vacuum pump); ir (CHCl3) 5.85μ; nmr δ 1.22 (pair of t, J=7.OHz, broad), 4.37 (quartet, 4).

Provenance & Evidence