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

Participants

Reaction Conditions

Reaction Steps

7-bromo-4-chloro-2-phenyl-thieno[3,2-c]pyridine 95 (130 mg, 0.40 mmol) was azeotroped to dryness from benzene and dissolved in THF (11 mL). Upon cooling to −78° C., the solution was treated dropwise with n-BuLi (168 μl of a 2.5 M solution in hexane, 0.42 mmol). After 2 min, acetaldehyde (50 μl, 0.89 mmol) was added and the resultant solution was stirred at −78° C. for 1 h. After this time, the reaction mixture was warmed to 0° C., quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3×). The organic layers were dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 4:1) to give 96. 1H NMR (400 MHz, CDCl3) δ: 1.68 (d, J=6.5 Hz, 3H), 2.29 (bd, 1H), 5.22–5.29 (m, 1H), 7.38–7.49 (m, 3H), 7.69 (s, 1H), 7.73–7.78 (m, 2H), 8.13 (s, 1H). MS (EI) m/z (M+H+) 290.

Provenance & Evidence