反応 #425135

反応方程式

cyclopentene oxide

1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

n-butyl lithium

sodium hydrogencarbonate

boron trifluoride-ethyl ether

→

title compound

収率 33.0%

(1S*,2R*)-2-[1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]cyclopentanol

収率 33.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction solution was further stirred for 10 minutes
2. 2
   workup.STIRRINGthe reaction solution was stirred at −78° C. for 3 hours
3. 3
   抽出followed by extraction four times with ethyl acetate (20 mL)
4. 4
   乾燥The thus obtained organic layer was dried over anhydrous sodium sulfate
5. 5
   濃縮After vacuum concentration
6. 6
   その他the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:4)

実験手順

To a solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (3.04 g, 20.0 mmol) in THF (30 mL), n-butyl lithium (1.63 M solution in hexane; 12.7 mL, 20.7 mmol) was added dropwise at −78° C. for 7 minutes. The reaction solution was stirred for 30 minutes, and boron trifluoride-ethyl ether (3.14 mL, 25.0 mmol) was then added thereto. The reaction solution was further stirred for 10 minutes. Then, cyclopentene oxide (2.08 mL, 24.0 mmol) was added thereto, and the reaction solution was stirred at −78° C. for 3 hours. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (15 mL) was added, followed by extraction four times with ethyl acetate (20 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:4) to yield the title compound (1.54 g, 33%) in the form of a diastereomeric mixture as a colorless oil.

出典