反应详情

To a solution of 4-(4-Hydroxy-3-methoxy-phenyl)but-3-ene-2-one (4.402 g, 22.93 mmol) in N,N-dimethylformamide (28.5 mL) were added imidazole (1.71 g, 25.22 mmol) and tert-butyldimethylsilyl chloride (3.8 g; 25.22 mmol). The reaction was allowed to stir for 4 h, then diluted with ethyl acetate (300 mL) and washed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated aqueous sodium chloride (50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated at reduced pressure to give crude product. Column purification on silica (8:2 hexanes/ethyl acetate) afforded 4-{4-[(tert-butyl-dimethyl-silanyloxy)-methyl}-3-methoxy-phenyl}-but-3-ene-2-one (5.24 g, 73% yield) as a solid: 1H NMR (400 MHz, CDCl3): δ 7.32 (d, 2H), 6.92 (m, 2H), 6.78 (d, 1H), 6.53 (d, 2H), 3.78 (s, 3H), 2.28 (s, 3H), 0.92 (s, 9H), 0.16 (s, 6H).

1. washwashed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated aqueous sodium chloride (50 mL)
2. dry with materialThe organic layer was dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated at reduced pressure
5. customto give crude product
6. customColumn purification on silica (8:2 hexanes/ethyl acetate)