反応 #50449

反応方程式

sec-butyllithium

2-methoxy-N,N-diethyl-benzamide

tetramethylethylenediamine

propionaldehyde

→

6-(1-hydroxyethyl)-2-methoxy-N,N-diethyl-benzamide

溶媒

diethyl ether

tetrahydrofuran

反応条件

後処理

1. 1
   その他does not exceed -68° C
2. 2
   workup.ADDITIONWhen the addition
3. 3
   温度to warm slowly to room temperature
4. 4
   workup.STIRRINGis subsequently stirred for one hour
5. 5
   洗浄The organic phase is washed with 2N hydrochloric acid
6. 6
   乾燥with saturated sodium chloride solution, dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated by evaporation

実験手順

13.7 ml of sec-butyllithium (1.4M in cyclohexane/isopentane) are added dropwise to a solution of 5.2 g of 2-methoxy-N,N-diethyl-benzamide and 2.91 g of tetramethylethylenediamine in 50 ml of absolute tetrahydrofuran in such a manner that the temperature does not exceed -68° C. When the addition is complete, the reaction mixture is stirred at -78° C. for a further hour and then 2.5 ml of propionaldehyde are added. The reaction mixture is allowed to warm slowly to room temperature, is subsequently stirred for one hour and is diluted with 300 ml of diethyl ether. The organic phase is washed with 2N hydrochloric acid and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated by evaporation to yield 6-(1-hydroxyethyl)-2-methoxy-N,N-diethyl-benzamide in the form of a crude product.

出典