反応 #424899

反応方程式

sodium hydrogencarbonate

cyclopentene oxide

1-methylpyrazole

n-butyl lithium

→

title compound

収率 21.3%

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

収率 21.3%

溶媒

THF

反応条件

後処理

1. 1
   抽出followed by extraction with ethyl acetate (500 mL)
2. 2
   乾燥The thus obtained organic layer was dried over anhydrous sodium sulfate
3. 3
   濃縮After vacuum concentration
4. 4
   その他the residue was purified with silica gel chromatography (dichloromethane/methanol=97:3)

実験手順

To a solution of 1-methylpyrazole (13.4 g, 163 mmol) in THF (1 L), n-butyl lithium (1.63 M solution in hexane; 100 mL, 163 mmol) was added dropwise at −78° C. for 40 minutes. To the reaction solution, cyclopentene oxide (15.1 g, 179 mmol) was added at −78° C., and the reaction solution was stirred at room temperature for 20 hours. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (100 mL) 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 (dichloromethane/methanol=97:3) to yield the title compound (5.77 g, 21%) as a colorless oil.

出典