Hydrochloric Acid → HCID 67548083, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-7-chloro-2,2-dimethyl-indan-1-one (650 mg, 1.6 mmol) in methanol (20 mL) is added a 1N solution of HCl in diethyl ether (15 mL, 15 mmol). The reaction is permitted to stir for 30 minutes, at which time the reaction is cooled to 0° C. and diluted with saturated aqueous NaHCO3. The reaction mixture is then concentrated in vacuo to ca. one fourth of the original volume and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted two times with ethyl acetate. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:19) to furnish 7-chloro-3-(5-hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; 1H NMR (400 MHz, CD3OD) δ ppm 0.86 (s, 3 H), 1.41 (s, 3 H), 4.77 (dd, 2 H); 5.88 (s, 1 H), 7.01 (s, 1 H), 7.09 (s, 1 H), 7.45 (d, J=7.58 Hz, 1 H), 7.62 (d, J=7.83 Hz, 1 H), 7.74 (t, J=7.71 Hz, 1 H); HRMS: (ESI) m/z 291.0898 [(M+H)+: Calcd for C15H16N2O2Cl: 291.0900].

Provenance & Evidence