Imidazole → HCID 12007215, compound

Participants

Reaction Steps

A solution of 2-(2-nitro-phenyl)ethanol (100 g, 590 mmol) in CH2Cl2 (800 mL), was treated with imidazole (117 g, 777 mmol) followed by tert-butyl-dimethylsilylchloride (562 g, 826 mmol). A white precipitate formed upon the addition and the reaction was stirred 2.5 hours. The mixture was filtered and diluted with CH2Cl2 (300 mL) and was washed with 0.1 N HCl (300 mL), H2O (400 mL), saturated aq NaHCO3 (400 mL), and brine (400 mL). The organic layer was dried over MgSO4, filtered and concentrated to give the title compound (160 g, 96%) 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 (H++1).

Provenance & Evidence