Reaktion #424891

Reaktionsgleichung

cyclohexene oxide

1-methylpyrazole

N,N,N′,N′-tetramethylethylenediamine

butyl lithium

→

title compound

Ausbeute 55.0%

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

Ausbeute 55.0%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle