S(Cl)(Cl)=O.[CH2:5]1[O:21][C:8]2([CH2:13][CH2:12][C:11](O)([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)[O:7][CH2:6]1.[OH-].[Na+]>N1C=CC=CC=1>[CH2:6]1[O:7][C:8]2([CH2:13][CH2:12][C:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][CH2:9]2)[O:21][CH2:5]1Thionyl chloride (10 mL) was added to a solution of 4-hydroxy-4-(3-pyridyl)cyclohexanone ethylene acetal (6.53 g. 27.8 mmol) in pyridine (60 mL) at −10° C. After stirring 0° C. for 30 min, the reaction mixture was poured onto ice. The aqueous layer was adjusted to pH 8 with 2M NaOH aq., and extracted with CH2Cl2, After drying and concentration, the crude product was purified by column chromatography (Hexane/EtOAc=2/1) to yield 4-(3-pyridyl)cyclohex-3-en-1-one ethylene acetal (4.85 g, 62%) as colorless oil.
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