3-Ethylaniline → (2,2-Diethoxyethyl)-(3-ethylphenyl)amine

関与物質

反応手順

To a 250-mL round bottom flask was added 3-ethylaniline (10.1 g, 83.2 mmol), bromoacetaldehyde diethyl acetal (10.8 g, 54.8 mmol) and sodium bicarbonate (7.04 g, 83.8 mmol) in absolute ethanol (40 mL). The resulting mixture was stirred at reflux for 5 d. The mixture was concentrated, diluted with ether (30 mL) and washed with water (2×60 mL). The organic solution was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by flash chromatography (SiO2, 5% then 15% EtOAc/hexanes) to give the title compound (4.5 g, 75%) as a white solid. 1H NMR (DMSO-d6) δ 6.98 (m, 1H), 6.42 (m, 2H), 5.34 (m, 1H), 4.53 (m, 1H), 3.59–3.35 (m, 4H), 3.19 (m, 2H), 2.41 (m, 2H), 1.17 (m, 9H).

情報源と証拠