Diiodomethane → cis-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanol

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Under argon gas atmosphere, to a suspension of (2Z)-3-(2-methyl-2H-indazol-4-yl)prop-2-en-1-ol (60.0 mg, 0.319 mmol) in methylene chloride (3 mL) was added 1 M diethylzinc hexane solution (1.60 mL, 1.60 mmol) under ice-cooling and the mixture was stirred for 10 min. Diiodomethane (128 μL, 1.59 mmol) was added, and the mixture was stirred at room temperature for 2 hr. The reaction solution was diluted with saturated aqueous ammonium chloride solution and water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (40.5 mg, yield 63%).

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