Imidazole → 3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-5-methylaniline

Participants

Reaction Steps

To a solution of (3-amino-5-methylphenyl)methanol (prepared according to: Behrens, C.; Egholm, M.; Buchardt, O. Synthesis 1992, 12, 1235-1236, 750 mg, 5.47 mmol) in CH2Cl2 (25 mL) was added imidazole (447 mg, 6.56 mmol) then TBDMSCl (989 mg, 6.56 mmol) at room temperature. After 72 hours the mixture was diluted with H2O. The layers were separated and the aqueous extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (20% EtOAc/hexanes) gave 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-methylaniline as a clear oil. 1H-NMR (300 MHz, CDCl3) δ 6.58 (s, 1H), 6.50 (s, 1H), 6.40 (s, 1H), 4.60 (s, 2H), 3.60 (bs, 2H), 2.24 (s, 3H).

Provenance & Evidence