反应详情

温度

50 °C

To a solution of methyl 3-cyano-4-hydroxybenzoate (82 g, 463 mmol; J. Med. Chem., 2002, 45, 5769) in dimethylformamide (800 mL) was added 2-iodopropane (93 mL, 926 mmol) and potassium carbonate (190 g, 1.4 mol). The resulting mixture was heated at 50° C. for 16 h, at which time it was allowed to cool to room temperature. The reaction was filtered and the mother liquor diluted with 0.5 N sodium hydroxide (1 L). The resulting mixture was extracted with ether (2×1 L) and the organics washed with 1 N HCl (1 L) and brine (700 mL), dried (MgSO4) and concentrated to give 100 g (˜100%) of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate as a yellow solid.

1. temperatureto cool to room temperature
2. filtrationThe reaction was filtered
3. additionthe mother liquor diluted with 0.5 N sodium hydroxide (1 L)
4. extractionThe resulting mixture was extracted with ether (2×1 L)
5. washthe organics washed with 1 N HCl (1 L) and brine (700 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated