Diisopropylamine → 1,1'-Undecane-1,11-diyldicyclopropanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyl lithium in hexane (1.8M, 297 mL, 0.53 mol) was added drop wise to a solution of freshly distilled diisopropylamine (78.3 mL, 0.50 mol) in dry THF (400 mL) at −60° C. under nitrogen atmosphere. The reaction mixture was slowly warmed to −20° C. and stirred for 30 min. The reaction mixture was re-cooled to −78° C., DMPU (8.16 g, 0.06 mol) was added drop wise and stirred for 15 min. Then cyclopropane carbonitrile (34.17 g, 0.50 mol) was added drop wise over a period 30 min and stirred for 1 h. To the reaction mixture was added drop wise 1,11-dibromoundecane (40.0 g, 0.12 mol) in dry THF (40 mL) and continued stirring at −78° C. for 2 h. The reaction mixture was slowly allowed to reach room temperature and continued stirring over a period of 16 h. The resulting reaction mixture was quenched with saturated NH4Cl (1.0 L) at 0° C. and the reaction mixture was extracted with ethyl acetate (600 mL×2). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (5% ethyl acetate in petroleum ether) to give product as a pale yellow liquid 25 g (68.5%).

Provenance & Evidence