反应详情

温度

70 °C

To a solution of 2-methoxy-4-propylphenol (10.0 mmol; 1.6 mL), NaI (1.0 mmol; 150 mg), and K2CO3 (11.0 mmol; 1.52 g), under argon, in acetonitrile (20 mL) was added tosyl chloride (10.5 mmol; 2.0 g). The reaction mixture was stirred at 70° C. for 36 hr, then quenched with NaOH (0.1N; 3 mL), and extracted with ethyl acetate (2*10 mL). Combined organic phases were washed with saturated NaHCO3 sat. (5 mL), dried over MgSO4, concentrated in vacuo. The crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane) to yield the desired compound as a clear oil (2.13 g; 6.6 mmol; 66%).

1. customquenched with NaOH (0.1N; 3 mL)
2. extractionextracted with ethyl acetate (2*10 mL)
3. washCombined organic phases were washed with saturated NaHCO3 sat. (5 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe crude was chromatographed on silica gel (gradient cyclohexane/dichloromethane)