Reaktion #425111

Reaktionsgleichung

cyclohexanone

1-methylpyrazole

N,N,N′,N′-tetramethylethylenediamine

butyl lithium

→

title compound

Ausbeute 86.0%

1-(1-Methyl-1H-pyrazol-5-yl)cyclohexanol

Ausbeute 86.0%

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 (250 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 (hexane/ethyl acetate=3:2)

Vorschrift

To a solution of 1-methylpyrazole (6.0 g, 73.1 mmol) and N,N,N′,N′-tetramethylethylenediamine (10.96 mL, 73.1 mmol) in THF (125 mL), butyl lithium (2.69 M solution in hexane; 31.8 mL, 85.5 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 30 minutes. Then, cyclohexanone (9.06 mL, 87.7 mmol) was added thereto, and the mixture was stirred at room temperature for 15 hours. To the reaction solution, water (500 mL) was added, followed by extraction with ethyl acetate (250 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=3:2), to yield the title compound (11.32 g, 86%) as a colorless oil.

Quelle