Reaktion #157913

Reaktionsgleichung

Methyl iodide

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

NaH

→

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto reach room temperature
2. 2
   Sonstigequenched with water 10 mL
3. 3
   Extraktionextracted with dichloromethane (2×20 mL)
4. 4
   TrocknenThe combined organic phase was dried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo
6. 6
   Extraktionextracted with dichloromethane
7. 7
   TrocknenThe organic phase was dried (Na2SO4)
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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).

Quelle