Water → HCID 54285995, compound

Participants

Reaction Steps

Sodium hydride (2.4 g. washed free of oil) was treated with dimethyl sulphoxide (100 ml.) and warmed under nitrogen to 75°-80° C. for 35 minutes. The mixture was cooled to ambient temperature and a solution of diethyl cyanomethylphosphonate (17.7 g.) in dry tetrahydrofuran (100 ml.) added dropwise. The mixture was stirred for 30 minutes. A solution of the above ketone (13.4 g.) in a mixture of dimethyl sulphoxide (100 ml.) and tetrahydrofuran (100 ml.) was then added dropwise and stirred for 16 hours at room temperature. The product was poured into water (1000 ml.) and the mixture extracted with ether (5×100 ml.). The combined extracts were washed with saturated brine, dried over potassium carbonate, filtered and evaporated. Distilled in vacuo gave 8-cyanomethylenetetracyclo-[4,3,0,02,4,03,7 ]nonane, b.p. 138°-140° C./18 mm.

Provenance & Evidence