Trifluoroacetic anhydride → 6-ethyl-1H-indole

참여 물질

반응 단계

To a solution of trifluoroacetic anhydride (45 mL) in trifluoroacetic acid (45 mL) at 4° C. under N2 was added (2,2-diethoxyethyl)-(3-ethylphenyl)amine (11.47 g, 48.36 mmol). After stirring for 30 min, the cold mixture was diluted with trifluoroacetic acid (60 mL). The mixture was stirred at reflux for 2.5 d, concentrated and extracted with methylene chloride (3×100 mL). The combined organic layers were washed with saturated NaHCO3 (3×60 mL), saturated NaCl (60 mL), dried (MgSO4) and concentrated. Flash chromatography (SiO2, 25% EtOAc/hexanes) gave the title compound (1.6 g, 23%) as a brown crystalline solid. 1H NMR (CDCl3) δ 8.03 (bs, 1H), 7.57 (m, 1H), 7.18 (s, 1H), 7.12 (m, 1H), 6.68 (m, 1H), 6.46 (m, 1H), 2.73 (m, 2H), 1.26 (m, 3H)

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