Water → N-Ethyl-2,6-dimethylaniline

Participants

Reaction Steps

Sodium borohydride (19.0 g, 0.5 mol) was added in small portions to a stirred solution of N-ethylidene-2,6-dimethylaniline (36.3 g, 0.247 mol) in THF (150 mL) and methanol (150 mL). The reaction was exothermic and a water/ice bath was used to cool the mixture. After addition of sodium borohydride, the bath was removed and the mixture was allowed to react for another 30 min. Then, water (150 mL) was added to the reaction mixture, while stirring and cooling the mixture with a water/ice bath. The volatiles were removed in vacuo, the aqueous layer extracted with dichloromethane (3×150 mL) and the combined organic layers were dried with sodium sulfate. Filtration and rotatory vaporation of the volatiles yielded the desired product. Yield: 36.4 g (99%).

Provenance & Evidence