反応 #928146

反応方程式

sodium chloride

ethyl salicylate

sodium hydride

ethyl 4-bromobutyrate

→

ethyl 4-(2-ethoxycarbonylphenyloxy)butyrate

収率 97.2%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONby adding dropwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 4.5 hours
3. 3
   workup.WAITat 65-70° C. for 2 hours
4. 4
   抽出extracted twice with ethyl acetate
5. 5
   洗浄the extract solution was washed twice with a 5% aqueous sodium chloride solution
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   その他the resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:95)

実験手順

A mixture of ethyl salicylate (10.0 g, 60.2 mmol), 60% sodium hydride (2.41 g, 60.2 mmol) and N,N-dimethylformamide (150 ml) w as stirred at room temperature for about 1 hour, followed by adding dropwise thereto ethyl 4-bromobutyrate (12.9 g, 66.2 mmol). The reaction mixture was stirred at room temperature for 4.5 hours and then at 65-70° C. for 2 hours. The reaction mixture was poured into a cooled 5% aqueous sodium chloride solution and extracted twice with ethyl acetate, and the extract solution was washed twice with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:95) to obtain 16.4 g of ethyl 4-(2-ethoxycarbonylphenyloxy)butyrate.

出典