反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 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).
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)
The suspension was filtered through Celite
the cake rinsed with fresh ethanol (400 mL)
the combined filtrate concentrated in vacuo
The resulting suspension was treated with dichloromethane (200 mL) and water (200 mL)
the layers separated
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
concentrated in vacuo
Kugelrohr distillation (0.1 torr, 120° C.)
来源 ID: ord-ae8bf134731b45fe977a2f0cf60ea28e