Imidazole → HCID 12007215, compound

Participants

Reaction Steps

A solution of 2-(2-nitro-phenyl)ethanol (10 g, 59 mmol) in CH2Cl2 (100 mL), was treated with imidazole (11.72 g, 77.7 mmol) followed by tert-butyl-dimethylsilylchloride (5.62 g, 82.6 mmol). A white precipitate formed upon the addition and the reaction was stirred 2.5 hours. The mixture was filtered and diluted with CH2Cl2 (100 mL) and was washed with 0.1 N HCl, H2O, saturated aq NaHCO3, and brine. The organic layer was dried over MgSO4, filtered and concentrated to give a transparent oil which was placed under high vacuum overnight to give the title compound (16.8 g, 100%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) −0.11 (s, 6H), 0.77 (s, 9H), 3.03 (t, J=6 Hz, 2H), 3.79 (t, J=6 Hz), 7.42–7.54 (m, 2H), 7.62 (ddd, J=<1, 6, 7 Hz, 1H), 7.88 (dd, J=<1, 7 Hz, 1H). MS (electrospray, m/z) 282 (M++1).

Provenance & Evidence