N,N-Dimethylaniline → HCID 86746455, compound

Participants

Reaction Steps

To a solution of 23.1 g (115 mmol, 2.42 eq) of benzyloxymethyl bromide in 40 ml of methylene chloride at 0° C. was added 15.6 ml (123 mmol, 2.60 eq) of N,N-dimethylaniline and a solution of 24.9 g (47.4 mmol, 1.0 eq) of intermediate 3A in 50 ml of methylene chloride. This mixture was brought immediately to ambient temperature and stirred for 18 hours. The reaction mixture was then diluted with 400 ml of ethyl acetate, washed sequentially with saturated aqueous copper sulfate (1×200 ml, 1×75 ml) and brine (1×150 ml), dried with magnesium sulfate and concentrated. The product was isolated by elution from silica gel with 10% ethyl acetate in hexanes, yielding 29.4 g (96.1%) of intermediate 3B as a clear, colorless, viscous oil.

Provenance & Evidence