반응 #87169

반응 방정식

NH4Cl

MeLi

ethyl 4-oxocyclohexanecarboxylate

→

ethyl 4-hydroxy-4-methylcyclohexanecarboxylate

수율 41.0%

용매

diethyl ether

반응 조건

후처리

1. 1
   추출the resulting mixture was extracted with EtOAc (100 mL×2)
2. 2
   세척The combined organic layers were washed with brine (150 mL) and water (150 mL)
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   농축concentrated
5. 5
   기타The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1)

실험 절차

To a solution of ethyl 4-oxocyclohexanecarboxylate (4.00 g, 23.5 mmol) in diethyl ether (80 mL) was added MeLi (37.6 mL, 1M in diethyl ether) at −60° C. under nitrogen atmosphere. The reaction mixture was stirred at −60° C. for 30 min. Saturated aqueous NH4Cl (50 mL) was added and the resulting mixture was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (150 mL) and water (150 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1) to afford ethyl 4-hydroxy-4-methylcyclohexanecarboxylate (1.8 g, 41% yield) as an oil.

출처