Imidazole → 4-[(tert-Butyldimethylsilyl)oxy]-N-methylaniline

Participants

Reaction Steps

A solution of 4-(methylamino)phenol (5.0 g, 29 mmol), TBDMSCl (4.8 g, 32 mmol) and imidazole (9.9 g, 0.15 mol) in DCM was stirred at r.t. for 1 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated and purified by silica gel chromatography (PE:EtOAc=10:1) to give 3.0 g (43%) of the title compound as a dark green oil. [M+H] Calc'd for C13H23NOSi, 238. Found, 238.

Provenance & Evidence