反应详情

温度

0 °C

A solution of nBuLi in hexanes (1.7 M, 14 mL, 24 mmol) was added over 15 min to a solution of 3,5-dimethoxytoluene (2.93 mL, 20 mmol) in THF (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h then at room temperature for 3 h. The reaction was cooled to 0° C. and a solution of the 4-phenylbutylbromide (4.13 mL, 1.2 mmol) in toluene (15 mL) was added over 5 min. The reaction mixture was allowed to warm to room temperature and heated to 80° C. for 3-4 h. The reaction was quenched slowly with water and partitioned over Et2O (100 mL) and water (100 mL). The phases were separated and the aqueous phase was extracted with Et2O (3×100 mL). The pooled organics were washed with brine (120 mL), dried over Na2SO4, and concentrated under vacuum and the crude product was purified by flash chromatography (silica-gel, petroleum ether/EtOAc 200:1) to afford the product as a clear oil (4.6 g, 81%). 1H NMR (CDCl3): δ 1.53-1.67 (m, 4H), 2.31 (s, 3H), 2.60-2.64 (m, 4H), 3.76 (s, 6H), 6.34 (s, 2H), 7.13-7.22 (m, 5H).

1. waitat room temperature for 3 h
2. temperatureThe reaction was cooled to 0° C.
3. temperatureto warm to room temperature
4. temperatureheated to 80° C. for 3-4 h
5. customThe reaction was quenched slowly with water
6. custompartitioned over Et2O (100 mL) and water (100 mL)
7. customThe phases were separated
8. extractionthe aqueous phase was extracted with Et2O (3×100 mL)
9. washThe pooled organics were washed with brine (120 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under vacuum
12. customthe crude product was purified by flash chromatography (silica-gel, petroleum ether/EtOAc 200:1)