Reaktion #56899

Reaktionsgleichung

2-(4-amino-phenyl)-malonic acid diethyl ester

lithium aluminum hydride

→

2-(4-amino-phenyl)-propane-1,3-diol

Ausbeute 17.3%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was cooled to 10° C.
2. 2
   Sonstigequenched by the addition of hydrated sodium sulfate (2 g)
3. 3
   FiltrationThe mixture was filtered
4. 4
   Waschenthe solid was rinsed with tetrahydrofuran (10 ml)
5. 5
   EinengenThe combined filtrates were concentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform

Vorschrift

To a solution of 2-(4-amino-phenyl)-malonic acid diethyl ester (450 mg, 1.8 mmol) in anhydrous ether (20 ml), cooled at 0-10° C., was added lithium aluminum hydride (68 mg, 1.8 mmol). After stirring at room temperature for 2 hours, the reaction was cooled to 10° C. and quenched by the addition of hydrated sodium sulfate (2 g). The mixture was filtered and the solid was rinsed with tetrahydrofuran (10 ml). The combined filtrates were concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform to provide 2-(4-amino-phenyl)-propane-1,3-diol (52 mg, 17% yield).

Quelle