Reaktion #4833

Reaktionsgleichung

o-nitrophenylpyruvic acid

L-(-)-proline

sodium borohydride

→

racemic α-hydroxy-2-nitrobenzenepropanoic acid

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.STIRRINGthe resulting gum was stirred with 10% aqueous HCl (200 ml.) for 4.5 hours
3. 3
   FiltrationA small amount of solid was filtered

Vorschrift

L-(-)-proline (7.50 g., 65.1 mmol) and sodium borohydride (2.46 g., 65.1 mmol) were stirred in tetrahydrofuran under nitrogen for sixteen hours. Recrystallized o-nitrophenylpyruvic acid (14.17 g., 76.5 mmol) in tetrahydrofuran (50 ml.) was added dropwise, and the resulting solution was stirred at room temperature for six days. The solvent was evaporated and the resulting gum was stirred with 10% aqueous HCl (200 ml.) for 4.5 hours. A small amount of solid was filtered to provide nearly racemic α-hydroxy-2-nitrobenzenepropanoic acid, 1.25 g., m.p. 98°-102° C., [α]D25 -4.21° (c 2.045, EtOH).

Quelle