Water → N-(2-((tert-butyldimethylsilyl)oxy)ethyl)aniline

Participants

Reaction Steps

To a stirred solution of 2-(phenylamino)ethanol (10 g, 72.9 mmol, Eq: 1.00) in dichloromethane (200 ml) were added diisopropylethylamine (13.2 g, 17.8 ml, 102 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (11.0 g, 72.9 mmol, Eq: 1.00) at room temperature under a nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (200 ml) and the organic layer was separated, washed with brine, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain N-(2-(tert-butyldimethylsilyloxy)ethyl)aniline (46) (8.45 g, 33.6 mmol, 46.1% yield).

Provenance & Evidence