O.C1O[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4]C1.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(C(O)=O)(F)(F)F>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:12]=1
Water (1 mL) was added to a cod solution of 4-(3-pyridyl)cyclohexanone ethylene acetal (4.79 g, 21.9 mmol) in CF3CO2H (20 mL). After stirring room temperature for 6 h, the reaction mixture was added dropwise to sat. NaHCO3. aq. The resulting mixture was adjusted to pH 8 with 2M NaOH aq. and extracted with CH2Cl2, After drying and consentration, the crude product was purified by column chromatography (Hexane/EtOAc=1/1→0/1) to yield 4-(3-pyridyl)cyclohexanone (3.23 g, 84%) as a colorless powder.
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