Diisopropylamine → HCID 15084248, compound

Participants

Reaction Steps

20.40 g (0.20 mol) of diisopropylamine were placed in 200 ml dry THF under nitrogen and 80 ml n-butyl lithium in hexane (2.5 M) were added dropwise. It was allowed to stir for 20 minutes and then 20.00 g (0.20 mol) of 1-methyl-2-pyrrolidinone were added dropwise at −78° C. After stirring the reaction mixture for 1 hour 17.64 g (0.20 mol) of dry ethyl acetate were added at −78° C. The reaction mixture was warmed to room temperature and stirred for 14 hours. The THF was removed on a rotary evaporator under reduced pressure and the residue was taken up in 80 ml of 6 N HCl. The acidic aqueous phase was saturated with NaCl and extracted 5 times with 300 ml ethyl acetate. The combined organic layers were dried over Na2SO4, and the solvent was removed on a rotary evaporator. The remaining yellow oil was purified by column chromatography. This gave 5.10 g product as a light yellow oil.

Provenance & Evidence