反応 #2271675

反応方程式

water

1,3-dibromopropane

3-hydroxy-4-methoxybenzophenone

sodium hydride

dimethylformamide

→

3-(3-bromopropoxy-4-methoxyphenyl]phenylmethanone

反応条件

後処理

1. 1
   その他At the end of the reaction
2. 2
   抽出extracted with ethyl acetate (400 ml)
3. 3
   洗浄The ethyl acetate solution was washed with water, brine
4. 4
   乾燥dried over anhydrous MgSO4
5. 5
   その他The solvent was removed
6. 6
   その他the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g: eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane:dichloromethane, 1.4 l)
7. 7
   その他The pure product thus obtained
8. 8
   その他Recrystallization twice from isopropyl ether (500 ml)

実験手順

A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide, (35 ml) was treated with sodium hydride (600 mg, 25 Mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for 2 hours. At the end of the reaction, the mixture was poured into water (500 ml) and extracted with ethyl acetate (400 ml). The ethyl acetate solution was washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed and the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g: eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane:dichloromethane, 1.4 l). The pure product thus obtained weighed 4.67 g, (66%) as an oil. Recrystallization twice from isopropyl ether (500 ml) gave analytically pure 3-(3-bromopropoxy-4-methoxyphenyl]phenylmethanone (2.42 g), m.p.=81°-83° C.

出典