반응 #424891

반응 방정식

cyclohexene oxide

1-methylpyrazole

N,N,N′,N′-tetramethylethylenediamine

butyl lithium

→

title compound

수율 55.0%

(1S*,2R*)-2-(1-Methyl-1H-pyrazol-5-yl)cyclohexanol

수율 55.0%

용매

THF

water

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 15 hours
2. 2
   추출followed by extraction with ethyl acetate (500 mL)
3. 3
   건조The thus obtained organic layer was dried over anhydrous sodium sulfate
4. 4
   농축After vacuum concentration
5. 5
   기타the residue was purified with silica gel chromatography (ethyl acetate)

실험 절차

To a solution of 1-methylpyrazole (9.34 g, 114 mmol) and N,N,N′,N′-tetramethylethylenediamine (17.1 mL, 114 mmol) in THF (300 mL), butyl lithium (1.63 M solution in hexane; 81.7 mL, 133 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 30 minutes. Then, cyclohexene oxide (13.9 mL, 137 mmol) was added thereto, and the mixture was stirred at room temperature for 15 hours. To the reaction solution, water (1 L) was added, followed by extraction with ethyl acetate (500 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate) to yield the title compound (11.2 g, 55%) as a colorless solid.

출처