Reaktion #57343

Reaktionsgleichung

phenylacetaldehyde

2-phenylethylamine

sodium triacetoxy-borohydride

→

compound D

Ausbeute 11.0%

Diphenethylamine

Ausbeute 11.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution is quenched with aq. saturated sodium bicarbonate (200 mL)
2. 2
   Extraktionextracted with EtOAc (4×100 mL)
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1)

Vorschrift

To a solution of phenylacetaldehyde (6.0 g, 50 mmol) and 2-phenylethylamine in THF (200 mL) is added sodium triacetoxy-borohydride drop wise. The solution is stirred under nitrogen overnight at room temperature. The solution is quenched with aq. saturated sodium bicarbonate (200 mL), and extracted with EtOAc (4×100 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1) to provide 1.25 g (11%) of the compound D as a clear oil. M+H+=226.10.

Quelle