Reaction #1195

Reaction equation

ethanolamine

ethanol

ethanol

butyl 12-(2,3-epoxypropoxy)-dodecanate

→

title compound

Yield 55.4%

butyl 12-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]dodecanate

Yield 55.4%

Solvents

water

Conditions

Workup

1. 1
   OtherA 100-ml flask equipped with a stirrer
2. 2
   workup.ADDITIONwas added to the reaction mixture
3. 3
   Extractionfollowed by extraction with chloroform
4. 4
   ConcentrationThe resultant chloroform solution was concentrated under reduced pressure
5. 5
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 100-ml flask equipped with a stirrer and dropping funnel was charged with 23.7 g (250 mmol) of ethanolamine and 23.7 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 8.20 g (25 mmol) of butyl 12-(2,3-epoxypropoxy)-dodecanate was added dropwise over 1 hour. After completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The resultant chloroform solution was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 5.40 g (yield: 55.4%) of the title compound (Ia-15).

Source