반응 #4833

반응 방정식

o-nitrophenylpyruvic acid

L-(-)-proline

sodium borohydride

→

racemic α-hydroxy-2-nitrobenzenepropanoic acid

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

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