Reaction #1206

Reaction equation

ethanolamine

1-tetradecyloxy-3-methyl-2-butene oxide

→

title compound

Yield 58.0%

3-(2-hydroxyethylamino)-4-tetradecyloxy-2-methyl-2-butanol

Yield 58.0%

Solvents

ethanol

ethanol

Conditions

Workup

1. 1
   OtherA 100-ml two-necked flask equipped with a stirrer and a dropping funnel
2. 2
   TemperatureWhile heating
3. 3
   TemperatureAfter heating
4. 4
   workup.STIRRINGstirring the mixture further for 16 hours
5. 5
   Otherthe resultant reaction mixture
6. 6
   Concentrationwas concentrated under reduced pressure
7. 7
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 100-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 15.3 g (16.7 mmol) of ethanolamine and 5.0 g of ethanol. While heating and stirring the mixture at 80° C. in a nitrogen atmosphere, an ethanol solution of 5.00 g (16.7 mmol) of 1-tetradecyloxy-3-methyl-2-butene oxide was added dropwise over 3 hours. After heating and stirring the mixture further for 16 hours, the resultant reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 3.47 g (yield: 58%) of the title compound (IIc-4).

Source