Imidazole → 3-((Tert-butyldimethylsilyl)oxy)aniline

Participants

Reaction Steps

3-Aminophenol (21.8 g, 0.200 mol) and imidazole (34 g, 0.50 mol) were dissolved in DMF (200 mL), the solution was cooled with an ice-water bath, and TBDMSCl (36.1 g, 0.24 mol) was added in one portion. The cooling bath was removed, the reaction mixture was allowed to warm-up to room temperature, and stirred for 1 h. DMF (ca. 150 mL) was evaporated in vacuo at +55° C., the residue was diluted with AcOEt (250 mL), washed with sat. aq. NaHCO3 (twice), water (several times), brine and dried over MgSO4. After evaporation of solvents, the oily residue was dried in vacuo (0.5 Torr) to a constant weight. Purification by column chromatography (gradient elution with hexane to hexane/ether=5/1) afforded compound 2 (Rf=0.24 in hexane/ether=8/1) as a clear oil (34.1 g, 76%). 1H NMR (300 MHz, CDCl3): δ=0.21 (s, 6 H, SiMe2But), 0.99 (s, 9 H, SiMe2But), 3.60 (br. s, 2 H, NH2), 6.18 (m, 1 H), 6.28 (m, 2 H), 6.98 (m, 1 H) ppm.

Provenance & Evidence