反应详情

1-benzyl-6-methyl-2-oxo-1,2-dihydropyridin-4-yl 4-bromobenzenesulfonate (3.0 mmol, 1.3 g), N,N′-dimethylformamide (30 mL), 3-chlorobenzyl alcohol (3.0 mmol, 0.43 g), and sodium hydroxide (60%, 3.3 mmol, 0.13 g) were stirred at room temperature under nitrogen for 4 hours. Hydrochloric acid (1 N, 10 mL) was added and the mixture extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine. After drying over magnesium sulfate and concentrating, the mixture was purified by flash column chromatography eluting with ethyl acetate:hexanes (1:1) to obtain a light yellow oil. (14.3 g, 64%): 1H NMR (DMSO-d6/300 MHz) δ: 7.4-7.0 (m, 10H), 6.0-5.8 (m, 2H), 5.2 (s, 2H), 5.0 (s, 2H), 2.1 (s, 3H). ES HRMS m/z 340.110 (M+H, C20H18NO2Cl requires 340.110).

1. extractionthe mixture extracted with ethyl acetate (3×25 mL)
2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine
3. dry with materialAfter drying over magnesium sulfate
4. concentrationconcentrating
5. customthe mixture was purified by flash column chromatography
6. washeluting with ethyl acetate:hexanes (1:1)
7. customto obtain a light yellow oil