Hydrochloric Acid → HCID 59199340, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-4-chloro-2,2-dimethyl-indan-1-one (2.4 g, 5.9 mmol) in methanol (40 mL) is added a 4N solution of HCl in 1,4-dioxane (9 mL, 36 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 4-chloro-3-(5-hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; HRMS: (ESI) m/z 291.0909 [(M+H)+: Calcd for C15H16N2O2Cl: 291.0909]; 1H NMR (400 MHz, CD3OD) δ ppm 0.91 (s, 3 H), 1.40 (s, 3 H), 4.80 (d, J=4.29 Hz, 2 H), 5.88 (s, 1 H), 6.89 (s, 1 H), 6.97 (s, 1 H), 7.69 (t, J=7.71 Hz, 1 H), 7.79-7.87 (m, 2 H).

Provenance & Evidence