反应详情

Add 5-chloromethyl-2-chloropyridine (4.12 g, 25.4 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (4.94 g, 25.4 mmol) in dimethylformamide (40 mL). After 10 minutes add potassium carbonate (5.27 g, 38.1 mmol) and cesium carbonate (8.28 g, 25.4 mmol). Stir at room temperature for one hour, and then heat to 70° C. for 2 hours. Cool, partition between ethyl acetate (300 mL) and water (300 mL). Wash twice with water, brine, dry, and concentrate. Dissolve the crude solid in dichloromethane, and add hexane (70 mL) slowly. Triturate and filter to afford the title compound as an orange powder (2.95 g, 36%): 1H NMR (CDCl3) δ 0.94 (t, 3H), 1.55 (sextet, 2H), 2.58 (s, 3H), 2.67 (t, 2H), 5.14 (s, 2H), 6.47 (d, 1H), 7.38 (d, 1H), 7.60 (d, 1H), 7.73 (d, 1H), 8.47 (s, 1H), 12.75 (s, 1H).

1. temperatureheat to 70° C. for 2 hours
2. temperatureCool
3. custompartition between ethyl acetate (300 mL) and water (300 mL)
4. washWash twice with water, brine
5. customdry
6. concentrationconcentrate
7. dissolutionDissolve the crude solid in dichloromethane
8. additionadd hexane (70 mL) slowly
9. customTriturate
10. filtrationfilter