反应详情

To a Parr bottle flushed with nitrogen was added ~1.0 g of Raney Nickel (50% suspension in H2O), ethanol (125 mL), ammonium hydroxide (30 mL), and a solution of 4-(3-methoxyphenyl)butyronitrile (8.49 g, 48.4 mmol) in ethanol (150 mL). The bottle was charged with hydrogen (60 psi) and rocked 3 d. The suspension was filtered through Celite, the cake rinsed with fresh ethanol (400 mL), and the combined filtrate concentrated in vacuo. The resulting suspension was treated with dichloromethane (200 mL) and water (200 mL), the layers separated, and the aqueous portion back-extracted with fresh dichloromethane (2×50 mL). The combined organic portions were washed with saturated sodium chloride solution (300 mL), dried (K2CO3), filtered, and concentrated in vacuo. Kugelrohr distillation (0.1 torr, 120° C.) provided the desired product as a clear liquid (6.77 g, 78%) which was identical spectroscopically to that previously reported. Venit, J. J.; DiPierro, M.; Magnus, P. J. Org. Chem. 1989, 54, 4298-4301. 1H NMR (CDCl3) δ 7.20 (t, J=8 Hz, 1H), 6.79-6.70 (m, 3H), 3.80 (s, 3H), 2.75-2.68 (m, 2H), 2.61 t J=8 Hz, 2H), 1.82-1.45 (m, 6H).

1. customTo a Parr bottle flushed with nitrogen
2. additionwas added ~1.0 g of Raney Nickel (50% suspension in H2O), ethanol (125 mL), ammonium hydroxide (30 mL)
3. filtrationThe suspension was filtered through Celite
4. washthe cake rinsed with fresh ethanol (400 mL)
5. concentrationthe combined filtrate concentrated in vacuo
6. additionThe resulting suspension was treated with dichloromethane (200 mL) and water (200 mL)
7. customthe layers separated
8. extractionthe aqueous portion back-extracted with fresh dichloromethane (2×50 mL)
9. washThe combined organic portions were washed with saturated sodium chloride solution (300 mL)
10. dry with materialdried (K2CO3)
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. distillationKugelrohr distillation (0.1 torr, 120° C.)