[C:1]([C:3]1([C:8]2[CH:9]=[C:10]([C:19]([O:21]CC)=[O:20])[CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[OH-].[Na+]>C1COCC1.CCO>[CH2:17]([O:16][C:14]([C:12]1[CH:11]=[C:10]([CH:9]=[C:8]([C:3]2([C:1]#[N:2])[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:13]=1)[C:19]([OH:21])=[O:20])=[O:15])[CH3:18]A solution of diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate (0.33 g, 1.05 mmol) and NaOH (1N in H2O, 0.945 mL, 0.945 mmol) in 5 mL THF and 5 mL EtOH was stirred at rt overnight. The reaction mixture was concentrated, diluted with H2O and extracted with ether. The aqueous phase was made acidic with 1N HCl, extracted with EtOAc and the combined organic layers were washed with brine. Drying and solvent evaporation gave 3-(ethoxycarbonyl)-5-(1-cyanocyclopentyl)benzoic acid. 1H NMR (400 MHz, CD3OD) δ 8.58 (m, 1H), 8.35 (m, 2H), 4.43 (q, J=7.1 Hz, 2H), 2.51 (m, 2H), 2.18 (m, 2H), 2.05 (m, 4H), 1.42 (t, J=7.1 Hz, 3H).
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