Water → 4-Cyclohex-1-en-1-yl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Participants

Reaction Steps

A solution of 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (J. Org. Chem. 2007, 72, 3589-3591; 2.00 g, 7.19 mmol), 2-cyclohex-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.50 g, 7.21 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (300 mg, 0.41 mmol) and potassium carbonate (3.00 g, 21.7 mmol) in DMF (13 mL) was stirred at 90° C. for 3 hours under microwave irradiation. After allowing to cool, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was washed twice with water (100 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with column chromatography (hexane/ethyl acetate=9:1) to yield the title compound (637 mg, 38%) as a colorless oil.

Provenance & Evidence