1-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol → 1-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

Participants

Reaction Steps

To a suspension of 1-(4-chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol 96 (92 mg, 0.32 mmol) and 168 mg of powdered 4 Å molecular sieves in dichloromethane (35 mL) was added TPAP (11 mg, 0.03 mmol). The resultant mixture was stirred at room temperature for 1 h. After this time, the reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium thiosulfate (1×) and saturated aqueous copper sulfate (1×). The organic layer was dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 17:3) to give 97. 1H NMR (400 MHz, CDCl3) δ: 2.79 (s, 3H), 7.40–7.53 (m, 3H), 7.75 (s, 1H), 7.78–7.83 (m, 2H), 8.83 (s, 1H). MS (EI) m/z (M+H+) 288.

Provenance & Evidence