Hydrochloric Acid → HCID 59199452, compound

Participants

Reaction Steps

To 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-2,2-dimethyl-indan-1-one (370 mg, 1 mmol) is added 4N HCl in 1,4-dioxane (20 mL, 0.80 mmol). The reaction is permitted to stir for 2 hours, at which time it is quenched with saturated aqueous NaHCO3 and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:20) to furnish 3-(5-Hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; HRMS: (ESI) m/z 257.1295 [(M+H)+: Calcd for C15H17N2O2: 257.1290]; 1H NMR (400 MHz, CDCl3) δ ppm 0.87 (s, 3 H), 1.46 (s, 3 H), 4.69-4.97 (m, 2 H), 5.93 (s, 1 H), 7.16 (s, 1 H), 7.19 (s, 1 H), 7.54 (d, J=7.6 Hz, 1 H), 7.65 (t, J=7.5 Hz, 1 H), 7.72-7.82 (m, 1 H), 7.93 (d, J=7.6 Hz, 1 H).

Provenance & Evidence