ethyl (+/-)-10,11-dihydro-3-methoxy-11-oxo-5H-dibenzo[a,d]cycloheptene-10-acetate → Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate
反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=O)[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=3[CH2:8][C:7]=2[CH:24]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=3[CH2:8][C:7]=2[CH:24]=1参加物
4
実験手順
A mixture of ethyl (±)-10,11-dihydro-3-methoxy-11-oxo-5H-dibenzo[a,d]cycloheptene-10-acetate (0.3 g., 0.93 mmol) and 10% Pd/C (0.3 g) in glacial acetic acid (25 mL) was hydrogenated at 50 psi for 18 hours. The mixture was filtered using celite® and washed with acetic acid. The filtrate was concentrated and reconcentrated from toluene and methylene chloride to give 0.25 g of the title compound: 1H NMR (400 MHz, CDCl3) δ 1.28 (t, 3H), 2.60 (m, 2H), 2.90 (m, 1H), 3.30 (m, 1H), 3.80 (s, 3H), 3.85 (d, 1H), 4.18 (q, 2H), 4.30 (d, 1H), 6.70 (m, 2H), 7.0 (d, 1H), 7.22 (m, 4H).