[Cl:1][C:2]1[C:11]([C:12]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[C:11]([C:12]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]Methyl 2-chloro-3-(1-cyanocyclobutyl)benzoate (710 mg, 2.84 mmol) was dissolved in a mixed solvent of tetrahydrofuran (9 mL)/methanol (3 mL)/water (3 mL), lithium hydroxide monohydrate (192 mg, 4.56 mmol) was added, and the mixture was stirred at room temperature for 19 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid (5 mL) was added dropwise to the residue. The precipitate was collected by filtration, and washed with water to give the title compound (435 mg, 65%) as a white powder.
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