Benzene → Heptopargil

Participants

Reaction Conditions

Reaction Steps

4.8 g (0.2 mole) of sodium hydride are added to 150 ml of dry benzene, and a solution of 33.4 g (0.2 mole) of (±)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one-oxime in 50 ml of dimethyl formamide is introduced into the mixture at 50° C. within 0.5 hours. When gas evolution ceases, the mixture is cooled to 25° C., and 23.8 g (0.2 mole) of propargyl bromide are added. The reaction is continued for an additional 2 hours. Thereafter the reaction mixture is shaken with water, the phases are separated, the benzene phase is evaporated, and the residue is subjected to fractional distillation in vacuo. 37.0 g (90.5%) of (±)-2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo[2,2,1]heptane are obtained as a light yellow oil; b.p.: 94°-96° C./1.5 mm Hg, nD20 =1.4953.

Provenance & Evidence