4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine → Cyclohexanone, 4-(4-pyridinyl)-
Reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3]C1>Cl.[Pd]>[N:13]1[CH:14]=[CH:15][C:10]([CH:7]2[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)=[CH:11][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4 g of 4-(4-pyridyl)cyclohex-3-enone ethylene acetal was dissolved in 70 ml of 0.5 N hydrochloric acid and 400 mg of 10% palladium/carbon was added thereto, to hydrogenate the starting compound at room temperature and atmospheric pressure. After the completion of the reaction, the catalyst was removed and the reaction mixture was made alkaline with an aqueous solution of sodium hydroxide and extracted with methylene chloride to thereby give 2.7 g of 4-(4-pyridyl)cyclohexanone. NMRδTMSCDCl3 : 1.7-2.3 (4H, m), 2.4-2.6 (4H, m), 2.8-3.2 (1H, M), 7.15 (2H, d) and 8.51 (2H, m).