Aluminium lithium hydride → [3-(2,2-Dimethyl-2,3-dihydro-benzofuran-3-yl)-3h-imidazol-4-yl]-methanol

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Reaction Steps

To a solution of 3-(2,2-dimethyl-2,3-dihydro-benzofuran-3-yl)-3H-imidazole-4-carboxylic acid methyl ester (2.2 g, 8.1 mmol), which can be prepared as described in Example 11, in THF (80 mL) at 0° C. is added LiAlH4 (310 mg, 8.1 mmol). After 30 minutes the reaction is quenched at 0° C. by the consecutive addition of 9:1 THF/H2O (3.5 mL), 2M aqueous NaOH (1.4 mL), and H2O (2.6 mL). The reaction is warmed to room temperature and diluted with THF (30 mL). After the addition of MgSO4 (3.75 g), the heterogeneous mixture is stirred for 15 min and then filtered through a pad of Celite®. The pad of Celite® is washed with ethyl acetate and the combined filtrate is concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:20) to afford 3-(2,2-dimethyl-2,3-dihydro-benzofuran-3-yl)-3H-imidazol-4-yl]-methanol; HRMS: (ESI) m/z 245.1296 [(M+H)+: Calcd for C14H17N2O2: 245.1290]; 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (s, 3 H), 1.54 (s, 3 H), 4.57-4.87 (m, 2 H), 5.60 (s, 1 H), 6.81-7.06 (m, 4 H), 7.22 (d, J=7.45 Hz, 1 H), 7.34 (t, J=7.45 Hz, 1 H).

Provenance & Evidence