反応 #577248

反応方程式

sodium iodide

2-(4-benzyloxy-phenyl)-ethanol

triethylamine

mesylchloride

→

1-Benzyloxy-4-(2-iodo-ethyl)-benzene

溶媒

ethyl acetate

methylene chloride

反応条件

後処理

1. 1
   その他to rise to room temperature
2. 2
   抽出The reaction mixture is extracted with methylene chloride (2×300 ml)
3. 3
   洗浄the combined organic layers are then washed with brine (2×300 ml)
4. 4
   濃縮concentrated under vacuum
5. 5
   workup.STIRRINGthe reaction mixture is stirred
6. 6
   温度under reflux for 6 hours
7. 7
   ろ過After filtration
8. 8
   洗浄the organic layer is washed with brine (3×400 ml)
9. 9
   乾燥dried with Na2SO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated under vacuum

実験手順

To a solution of 2-(4-benzyloxy-phenyl)-ethanol (78.72 g, 0.34 mol) in methylene chloride (400 ml) is added triethylamine (67.3 ml, 0.44 mol, 1.4 eq), then at 0° C. is added mesylchloride (34.8 ml, 0.44 mol, 1.3 eq). The reaction mixture is stirred at 0° C. for 30 minutes and allowed to rise to room temperature. The reaction mixture is extracted with methylene chloride (2×300 ml), the combined organic layers are then washed with brine (2×300 ml) and concentrated under vacuum. To the crude product in solution in ethyl acetate (600 ml) is added sodium iodide (67.2 g, 0.44 mol, 1.3 eq) and the reaction mixture is stirred under reflux for 6 hours. After filtration, the organic layer is washed with brine (3×400 ml), dried with Na2SO4, filtered and concentrated under vacuum. 1-Benzyloxy-4-(2-iodo-ethyl)-benzene is isolated after crystallization with diethyl ether (116.5 g, 86%).

出典