Methyl vinyl ketone → 4-(3-Chloropyridin-2-yl)-4-methylcyclohex-2-enone

反応式

[Cl:1][C:2]1[C:3]([CH:8]([CH3:11])[CH:9]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH:14]([C:16]([CH3:18])=[O:17])=[CH2:15]>C(OCC)C>[Cl:1][C:2]1[C:3]([C:8]2([CH3:11])[CH2:15][CH2:14][C:16](=[O:17])[CH:18]=[CH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

実験手順

To a 0° C. solution of the product of Example 38D (0.71 g, 4.19 mmol) in diethyl ether (10 mL) was added a solution of potassium hydroxide (3M in methanol, 0.56 mL, 1.68 mmol), followed by methyl vinyl ketone (0.47 g, 0.55 mL, 6.70 mmol). The reaction was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was diluted with diethyl ether, and washed with water and brine. The organic layer was concentrated, and the residue was chromatographed on silica gel eluting with 25% ethyl acetate-hexane to give the title compound (0.20 g, 22%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.53 (dd, J=1.5, 4.6, 1H), 7.92 (dd, J=1.5, 8.0, 1H), 7.45-7.26 (m, 2H), 5.92 (d, J=10.2, 1H), 2.82-2.67 (m, 1H), 2.64-2.52 (m, 1H), 2.31 (ddd, J=4.8, 7.2, 17.3, 1H), 2.12-2.00 (m, 1H). MS (DCI) m/z 222 (M+H)+.