Imidazole → 5-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-methylbenzenamine

Participants

Reaction Steps

To a solution of (3-amino-4-methylphenyl)methanol (1.0 g, 7.3 mmol) in DMF (7.3 mL) was added tert-butyldimethylchlorosilane (1.2 g, 8.1 mmol) and imidazole (0.65 g, 9.5 mmol). The reaction stirred at room temperature for 18 hours and then was poured into a separatory funnel with water and EtOAc. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-40% EtOAc/heptane) afforded the title compound.

Provenance & Evidence