Reaktion #82943

Reaktionsgleichung

sodium boron hydride

α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride

2,3-dimethoxybenzaldehyde

triethylamine

→

3,4-dimethoxybenzyl alcohol

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONafter adding
2. 2
   TemperaturThe mixture was heated
3. 3
   Temperaturunder reflux for 30 minutes
4. 4
   workup.STIRRINGwhile stirring under ice cooling
5. 5
   Einengenthe mixture was concentrated
6. 6
   Sonstigethe chloroform layer was collected
7. 7
   Waschenwashed with water
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off
10. 10
    Sonstigethe residue was recrystallized from ethyl acetate-n-hexane

Vorschrift

1.0 g of α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride was suspended in 5 ml of methanol, and after adding thereto 0.85 g of 2,3-dimethoxybenzaldehyde, 0.63 ml of triethylamine was added dropwise to the mixture while stirring at room temperature. The mixture was heated under reflux for 30 minutes, and 0.24 g of sodium boron hydride was added slowly to the mixture while stirring under ice cooling. After the foaming stopped, the mixture was concentrated. The residue was subjected to a separating procedure with chloroform and water, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 1.07 g of α-[[2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 96°-97° C.

Quelle