Imidazole → HCID 12007215, compound

Participants

Reaction Conditions

Reaction Steps

Add 2-nitrophenethyl alcohol (20 g, 120 mmol) and imidazole (11.4 g, 167 mmol) to dichloromethane (200 mL). Cooled to 0° C. and add solid tert-butyldimethylsilyl chloride (23.4 g, 155 mmol). Stir the mixture at 20° C. for 2 hours and dilute with 1:1 ethyl acetate:diethyl ether. Wash with distilled water, aqueous 3% acetic acid, aqueous 0.5 molar sodium hydrogen carbonate, and saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to give 32.4 g (96%) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.89 (dd, 1H, J=8.0, 1.2 Hz), 7.50 (dt, 1H, J=7.2, 1.6 Hz), 7.37 (m, 2H), 3.89 (t, 2H, J=6.4 Hz), 3.12 (t, 2H, J=6.4 Hz), 0.83 (s, 9H), 0.06 (s, 6H).

Provenance & Evidence