反应 #157913

反应方程式

Methyl iodide

2-iodo-4-(1-phenyl-cyclohexyl)-phenol

NaH

→

2-Iodo-1-methoxy-4-(1-phenyl-cyclohexyl)-benzene

溶剂

DMF

反应条件

后处理

1. 1
   其他to reach room temperature
2. 2
   其他quenched with water 10 mL
3. 3
   萃取extracted with dichloromethane (2×20 mL)
4. 4
   干燥The combined organic phase was dried (Na2SO4)
5. 5
   浓缩concentrated in vacuo
6. 6
   萃取extracted with dichloromethane
7. 7
   干燥The organic phase was dried (Na2SO4)
8. 8
   浓缩concentrated in vacuo

实验过程

NaH (60% in mineral oil, 60 mg, 1.50 mmol) was added an ice-cooled solution of 2-iodo-4-(1-phenyl-cyclohexyl)-phenol (400 mg, 1.06 mmol) in DMF (10 mL). Methyl iodide (125 μL, 2.0 mmol) was added. The reaction temperature was allowed to reach room temperature. The mixture was stirred for 2 h, then quenched with water 10 mL and extracted with dichloromethane (2×20 mL). The combined organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was taken up in water (20 mL) and extracted with dichloromethane. The organic phase was dried (Na2SO4) and concentrated in vacuo. 1H-nmr of the syrup (430 mg) indicated full conversion to the methyl ether. 1H NMR (400 MHz, CDCl3): 7.71 (d, 1H, J=2.1 Hz), 7.32-7.25 (m, 4H), 7.18 (dd, 1H, J=2.1 Hz, J=8.8 Hz), 7.17-7.13 (m, 1H), 6.72 (d, 1H, J=8.8 Hz), 3.83 (s, 3H), 2.32-2.18 (m, 4H), 1.62-1.44 (m, 6H).

来源