Sodium hydride → Ammonia

Beteiligte Stoffe

Reaktionsschritte

6 g of NaH (50% in paraffin) are added to a solution of 41.9 g of 2-[2-(2-p-toluenesulfonyloxymethyl-5-propylcyclohexyl)-ethyl]-valeronitrile (obtainable by reaction of p-propylbenzyl 2-tetrahydropyranyl ether with 2-propylsuccinic anhydride/AlCl3 to give 2-(2-tetrahydropyranyloxymethyl-5-propyl-benzoylmethyl)-valeric acid, hydrogenation to 2-[2-(2-tetrahydropyranyloxymethyl-5-propylcyclohexyl)-ethyl]-valeric acid, successive reactions with SOCl2 and NH3 to give 2-[2-(2-hydroxymethyl-5-propylcyclohexyl)-ethyl]-valeric acid amide, dehydration with dicyclohexylcarbodiimide to give the nitrile and tosylation) in 250 ml of dimethylsulfoxide, with stirring; during this addition, the temperature is kept below 35°. The mixture is stirred for a further 2 hours and worked up in the customary manner to give 2-cyano-2,6-dipropyl-trans-decalin.

Herkunft & Nachweise