反応 #1767

反応方程式

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

溶媒

DMF

反応条件

後処理

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice
2. 2
   抽出the resulting aqueous solution extracted with Et2O (3×200 mL)
3. 3
   乾燥The organic phase was dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   その他the Et2O removed under reduced pressure
6. 6
   その他The crude white solid was purified by pressurized silica gel column chromatography
7. 7
   その他Evaporation of the hexanes

実験手順

To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12 g, 46 mmol) in DMF (150 mL) was added NaH (2.76 g, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was allowed to warm to ambient temperature overnight with stirring. The reaction mixture was poured onto ice and the resulting aqueous solution extracted with Et2O (3×200 mL). The organic phase was dried (MgSO4), filtered and the Et2O removed under reduced pressure. The crude white solid was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-methoxybenzoate as a white powder.

出典