Réaction #1211

Équation de réaction

KOH

N2

N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide

LiAlH4

→

title compound

Rendement 62.0%

16-[N,N-bis(2-hydroxyethyl)amino]-1-hexadecanol

Rendement 62.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreA 500-ml flask equipped with a stirrer
2. 2
   Températurereflux condenser
3. 3
   workup.ADDITIONwere added
4. 4
   TempératureAfter cooling the reaction mixture to room temperature
5. 5
   Autrea salt deposited was separated by filtration
6. 6
   workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
7. 7
   Autrethe resultant residue was purified by column chromatography on silica gel

Mode opératoire

A 500-ml flask equipped with a stirrer and reflux condenser was charged with 3.01 g (79.3 mmol) of LiAlH4 and 200 ml of tetrahydrofuran. While stirring the mixture at room temperature in an N2 atmosphere, 5.00 g (13.9 mmol) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide were added, followed by stirring at 65° C. for 18 hours. After cooling the reaction mixture to room temperature, 15 g of 3% aqueous KOH were added, and a salt deposited was separated by filtration. The solvent was then distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 2.98 g (yield: 62%) of the title compound (IId-3).

Source