反应详情

Sodium bis(trimethylsilyl)amide (2 M in tetrahydrofuran (THF), 37.5 mL, 75.0 mmol) was slowly added to a solution of cyclopropanecarbonitrile (3.35 g, 49.9 mmol) in THF (30 mL) at room temperature. The reaction mixture was stirred for 20 minutes and then a solution 1-chloromethyl-4-methoxy-benzene (7.83 g, 50.0 mmol) in THF was added. The mixture was heated to reflux for 3 hours and then quenched with a saturated aqueous solution of ammonium chloride (50 mL). The separated aqueous layer was extracted three times with ethyl acetate (50 mL). The combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give crude 1-(4-methoxy-benzyl)-cyclopropanecarbonitrile, which was used directly in the next step.

1. temperatureThe mixture was heated
2. temperatureto reflux for 3 hours
3. customquenched with a saturated aqueous solution of ammonium chloride (50 mL)
4. extractionThe separated aqueous layer was extracted three times with ethyl acetate (50 mL)
5. washThe combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate
6. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness