反応 #1178422

反応方程式

(3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol

→

(1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol

収率 82.4%

溶媒

methanol

HCl

反応条件

後処理

1. 1
   ろ過filtered through Celite
2. 2
   洗浄The filter cake was washed with methanol (2×100 mL)
3. 3
   その他the filtrate was evaporated to dryness
4. 4
   workup.ADDITIONThe residue was treated with 5% aqueous NaOH (100 mL)
5. 5
   抽出extracted with ethyl acetate (2×200 mL)
6. 6
   乾燥The combined organic extracts were dried over Na2SO4
7. 7
   その他evaporated

実験手順

To a stirred solution of (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (5.87 g, 19.3 mmol) in methanol (40 mL) and concentrated HCl (10 mL), cooled to ˜5° C., was added zinc powder. The mixture was stirred at room temperature overnight and filtered through Celite. The filter cake was washed with methanol (2×100 mL) and the filtrate was evaporated to dryness. The residue was treated with 5% aqueous NaOH (100 mL) and extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over Na2SO4 and evaporated to leave (1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol (4.36 g) as a white solid. 1H NMR (500 MHz, CDCl3) δ (ppm): 7.25 (s, 1H), 7.185 (s, 2H), 4.21 (s, 1H), 1.55 (m, 4H), 1.3 (m, 3H), 1.1 (m, 3H).

出典