Water → HCID 11658740, compound

Participants

Reaction Steps

68.0 g (0.23 mol) of N-ethyl-N-[2-(methoxymethyl)oxyethyl]-4-bromoaniline was dissolved in 500 ml of anhydrous THF in an atmosphere of nitrogen, and 280 ml (2.2-fold equivalent weight) of a 1.7M n-butyllithium solution (solvent: n-pentane) was dropwise added thereto at -78° C., followed by stirring for 45 minutes. To the reaction solution obtained, 25 ml of anhydrous DMF was added, and the solution was stirred for 8 hours while allowing the temperature to naturally rise to room temperature. Thereafter, 100 ml of water was added to the resulting reaction solution, which was then extracted with dichloromethane (100 ml×2). The organic layer was dried with anhydrous sodium sulfate, and thereafter concentrated under reduced pressure. The residue thus obtained was distilled under reduced pressure to obtain 51.0 g of N-ethyl-N-[2-(methoxymethyl)oxyethyl]-4-formylaniline (yield: 91%).

Provenance & Evidence