Reaction #1207

Reaction equation

KOH

N-(9-octadecenoyl)ethanolamine

LiAlH4

N2

→

title compound

Yield 65.0%

2-(9-octadecenylamino)-1-ethanol

Yield 65.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherA 100-ml eggplant type flask equipped with a stirrer
2. 2
   TemperatureWhile heating
3. 3
   Otherthe resultant reaction mixture
4. 4
   Temperaturewas cooled to room temperature
5. 5
   OtherAfter a salt deposited was separated by filtration
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   Otherthe resultant residue was purified by column chromatography on silica gel

Procedure

A 100-ml eggplant type flask equipped with a stirrer was charged with 1.40 g (37.2 mmol) of LiAlH4 and 30 ml of tetrahydrofuran. While heating and stirring the contents at room temperature in an N2 atmosphere, a tetrahydrofuran solution of 1.67 g (5.12 mmol) of N-(9-octadecenoyl)ethanolamine was added dropwise over 10 minutes. After the mixture was heated to 60° C. and stirred for 16 hours, the resultant reaction mixture was cooled to room temperature, and 14 g of 5% aqueous KOH. After a salt deposited was separated by filtration, the filtrate was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 0.96 g (yield: 65%) of the title compound (IIc-6).

Source