Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol

Participants

Reaction Steps

To a solution of resorcinol (5.5 g, 50 mmol) in anhydrous DMF (15 mL) was added imidazole (7.14 g, 210 mol %) and tert-butyldimethylsilyl chloride (7.53 g, 105 mol %). The reaction mixture was stirred for 20 h. The reaction mixture was diluted with water (a white precipitate formed) and then it was extracted with ether (3×300 mL). The combined extract was dried (Na2SO4), filtered and concentrated to yield 5.4 g (48.3%) of the title compound; 1H-NMR (CDCl3) δ7.07 (t, 1 H, J=8.0), 6.42 (pseudot, 2 H, J=7.6), 6.36 (s, 1 H), 5.06 (bs, 1 H), 0.98 (s, 9 H), 0.20 (s, 6 H); 13C--NMR (CDCl3) δ157.90, 156.51, 129.89, 112.66, 108.42, 107.53, 25.61, 18.14, 14.49.

Provenance & Evidence