Hydrochloric Acid → HCID 59199345, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-6-chloro-2,2-dimethyl-indan-1-ol (400 mg, 0.98 mmol) in 1,4-dioxane (15 mL) is added manganese(IV) oxide (2.0 g, 20 mmol). The resulting heterogeneous solution is heated at 80° C. for 60 minutes, cooled to room temperature, filtered and concentrated. The resulting residue is then dissolved in methanol, cooled to 0° C. and treated with 4 N hydrochloric acid in 1,4-dioxane (1 mL, 4.0 mmol). The reaction is placed at room temperature and permitted to stir for 3 hours, 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 (ethanol-ethyl acetate, 0:1 to 1:10) to furnish 6-chloro-3-(5-hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; HRMS: (ESI) m/z 291.0891 [(M+H)+: Calcd for C15H16N2O2Cl: 291.0900]; 1H NMR (400 MHz, CDCl3) δ ppm 0.87 (s, 3 H), 1.44 (s, 3 H), 1.89 (br. s., 1 H), 4.70-4.92 (m, 2 H), 5.75 (s, 1 H), 6.92 (s, 1 H), 7.07 (s, 1 H), 7.41 (d, J=8.1 Hz, 1 H), 7.69 (dd, J=8.3, 2.0 Hz, 1 H), 7.87 (d, J=2.0 Hz, 1 H).

Provenance & Evidence