Diethylamine → Diethylamine

Participants

Reaction Steps

An ice-cold solution of diethylamine (3.48 g, 4.9 ml, 47.55 mmol, dried with KBr) in 10 ml of anhydrous ether was prepared. Next, 19.1 ml of a 2.5M solution of n-butyllithium in hexane was added to the diethylamine solution with stirring under a nitrogen atmosphere. After 10 minutes, a solution of 2,4,6-trimethyl-1,2-epoxynonane (6) (3.50 g, 19.0 mmol) in 10 ml of anhydrous ether was added to the reaction mixture and this mixture was refluxed for one hour. Progress of the reaction was checked by withdrawing samples, quenching with water, and analyzing by TLC. Reaction time was determined to ensure total consumption of the epoxide. Upon completion, the reaction mixture was cooled and poured into ice water. The organic layer was separated and the aqueous layer was saturated with solid sodium chloride and extracted with ether. The combined organic layers were washed with 1N hydrochloric acid, saturated sodium hydrogen carbonate solution, water, and brine. the solution was dried over sodium sulfate and solvent was removed in vacuo. Vacuum distillation at 85° -90° C. yielded 2-methylene-4,6-dimethylnonan-1-ol (7).

Provenance & Evidence