Reaction #50449

Reaction equation

sec-butyllithium

2-methoxy-N,N-diethyl-benzamide

tetramethylethylenediamine

propionaldehyde

→

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

Solvents

diethyl ether

tetrahydrofuran

Conditions

Workup

1. 1
   Otherdoes not exceed -68° C
2. 2
   workup.ADDITIONWhen the addition
3. 3
   Temperatureto warm slowly to room temperature
4. 4
   workup.STIRRINGis subsequently stirred for one hour
5. 5
   WashThe organic phase is washed with 2N hydrochloric acid
6. 6
   Dryingwith saturated sodium chloride solution, dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated by evaporation

Procedure

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.

Source