Ammonium Chloride → Cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

反応式

[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[C:12]=1[C:19]1[N:24]=[CH:23][C:22]([CH:25]=[O:26])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=1)[CH3:10].[Cl-].[NH4+]>CCOCC>[CH:1]1([CH:25]([C:22]2[CH:23]=[N:24][C:19]([C:12]3[C:13]([CH2:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:9][CH3:10])=[CH:20][C:21]=2[O:27][CH2:28][CH3:29])[OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

実験手順

A cyclohexylmagnesium chloride solution (2 M in THF, 1 mL) is slowly added to a solution of 6-(2,6-diethyl-phenyl)-4-ethoxy-pyridine-3-carbaldehyde (prepared as described D above) (142 mg, 0.5 mmol) in ether (2 mL) at 0° C., and the resulting mixture is stirred at room temperature for 30 minutes. Saturated ammonium chloride solution (1 mL) is added to quench the reaction. The organic layer is separated and dried over anhydrous Na2SO4. The solvents are removed in vacuo and the crude is purified with PTLC (hexanes/ethyl acetate 3:1) to give cyclohexyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol. 1H NMR: (CDCl3) 8.40 (s, 1H), 7.28 (t, 1H), 7.16 (d, 2H), 6.76 (S, 1H), 4.54 (t, 1H), 4.08 (q, 2H), 2.32 (m, 4H), 2.05 (br, 1H), 1.75 (m, 4H), 1.40 (m, 4H), 1.05 (m, 10H).