Reaktion #87099

Reaktionsgleichung

NaBH4

methyl 3-methyl-2-oxocyclopentanecarboxylate

→

methyl 2-hydroxy-3-methylcyclopentanecarboxylate

Ausbeute 82.7%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with saturated aqueous NH4Cl (500 mL)
2. 2
   Extraktionthe resulting mixture was extracted with EtOAc (250 mL×5)
3. 3
   WaschenThe combined organic phases were washed with brine (500 mL×2)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated

Vorschrift

NaBH4 (9.98 g, 0.260 mol) was added in portions to a solution of methyl 3-methyl-2-oxocyclopentanecarboxylate (41.2 g, 0.26 mol) in MeOH (250 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 5 h. The reaction was quenched with saturated aqueous NH4Cl (500 mL) and the resulting mixture was extracted with EtOAc (250 mL×5). The combined organic phases were washed with brine (500 mL×2), dried over anhydrous sodium sulfate, and concentrated to afford methyl 2-hydroxy-3-methylcyclopentanecarboxylate (34.0 g).

Quelle