CS(Cl)(=O)=O.[CH2:6]([O:13][CH2:14][C@H:15]1[CH2:17][C@@H:16]1[CH2:18]O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[C-:21]#[N:22].[K+]>C1COCC1>[CH2:6]([O:13][CH2:14][C@H:15]1[CH2:17][C@@H:16]1[CH2:18][C:21]#[N:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Methanesulfonyl chloride (443 μL, 5.72 mmol) was added to a solution of ((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)methanol (1.00 g, 5.20 mmol) and TEA (797 μL, 5.72 mmol) in THF (15 mL) at 0° C., and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water (80 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in DMF (15 mL), and potassium cyanide (0.677 g, 10.40 mmol) was added thereto at room temperature. The reaction mixture was stirred at 60° C. for 2 hr, and poured into water (100 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 17→38% ethyl acetate/hexane) to give 2-((1R,2S)-2-((benzyloxy)methyl)cyclopropyl)acetonitrile (782 mg, 3.89 mmol, 75%) as a colorless oil.
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