Reaction #1095846

Reaction equation

ethyl acrylate

ethyl glycinate hydrochloride

sodium hydroxide

→

Diethyl-2-azabutane-1,4-dicarboxylate

Solvents

water

Conditions

Workup

1. 1
   OtherAfter 19 h the solution was partitioned with dichloromethane (3×100 mL)
2. 2
   DryingThe organic layer was dried with anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   workup.DISTILLATIONThe residue was distilled
6. 6
   Otherto afford AA (28.8 g, 61%)

Procedure

A 4.7 M aqueous solution of sodium hydroxide (50 mL) was added into a stirred, ice-cooled solution of ethyl glycinate hydrochloride (32.19 g, 0.23 mole) in water (50 mL). Then, ethyl acrylate (23.1 g, 0.23 mole) was added and the mixture was stirred at room temperature until completion of the reaction was ascertained by TLC. After 19 h the solution was partitioned with dichloromethane (3×100 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and evaporated. The residue was distilled to afford AA (28.8 g, 61%).

Source