Reaction #1197

Reaction equation

11-(butyldimethylsilyl)undecyl glycidyl ether

ethanolamine

N2

ethanolamine

→

title compound

Yield 73.3%

1-(2-hydroxyethylamino)-3-[11-(butyldimethylsilyl)undecyloxy]-2-propanol

Yield 73.3%

Solvents

ethanol

ethanol

ethanol

Conditions

Workup

1. 1
   OtherA 100-ml two-necked flask equipped with a stirrer
2. 2
   workup.DISTILLATIONwere distilled off under reduced pressure
3. 3
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 100-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.58 g (75 mmol) of ethanolamine and 9.2 g of ethanol. The contents were heated to 80° C. with stirring in an N2 atmosphere, and an ethanol solution of 1.71 g (5 mmol) of 11-(butyldimethylsilyl)undecyl glycidyl ether was added dropwise to the contents over 1 hour. The resultant mixture was stirred further for 1 hour at 80° C. After completion of the reaction, ethanol and excess ethanolamine were distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 1.48 g (yield: 73%) of the title compound (Ia-18).

Source