反应 #1018873

反应方程式

bromide

4-(bromomethyl)benzophenone

sodium hydride

Diethyl malonate

→

1,3-diethyl 2-[(4-benzoylphenyl)methyl]propanedioate

收率 86.0%

溶剂

DMF

water

DMF

反应条件

后处理

1. 1
   其他was obtained
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 16 h at ambient temperature
3. 3
   萃取extracted with dichloromethane (3×50 mL)
4. 4
   其他The organic phase was separated
5. 5
   其他dried
6. 6
   其他evaporated to an oily residue

实验过程

60% mineral oil suspension of sodium hydride (1.454 g; 36.3 mmol) was added into anhydrous DMF (50 mL) under nitrogen at 0° C. Diethyl malonate (5.82 g; 36.3 mmol) was added to the stirred suspension over 10 min and the mixture was then stirred rapidly at 0° C. until a clear pale yellow solution was obtained. 4-(bromomethyl)benzophenone (5.00 g; 18.2 mmol) in DMF (15 mL) was added dropwise over 5 min and the reaction mixture was stirred for 16 h at ambient temperature. Complete conversion of the starting bromide was confirmed by TLC. The reaction was diluted with water (400 mL) and extracted with dichloromethane (3×50 mL). The organic phase was separated, dried and evaporated to an oily residue. Chromatography on silicagel (eluent hexane/2-butanone 10:1→5:1) provided the desired 1,3-diethyl 2-[(4-benzoylphenyl)methyl]propanedioate (5.47 g; 86%) as a colourless oil.

来源