3-(4-Benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester → 3-(4-Hydroxyphenyl)-2-(2-methoxy-phenoxy)-2-methyl-propionic acid ethyl ester
反応式
[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])([CH3:28])[CH:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20]CC2C=CC=CC=2)=[CH:16][CH:15]=1)OC(=O)C(F)(F)F)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:38])[C:5]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])([CH3:28])[CH2:6][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[CH3:2]参加物
4
実験手順
3-(4-Benzyloxy-phenyl)-2-(2-methoxy-phenoxy)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-propionic acid ethyl ester was dissolved in ethyl acetate (350 mL), treated with 5% palladium on carbon (8.77 g), and stirred under an atmosphere of hydrogen for 48 h. The suspension was filtered through celite and concentrated in vacuo. The residue was purified by flash column chromatography (25% ethyl acetate in hexanes) to provide the title compound as a light yellow oil (1.73 g, 25%). 1H NMR (400 MHz, CDCl3): δ 7.12 (d, 2H, J=6.65 Hz), 6.98–6.93 (m, 5H), 4.24–4.15 (m, 2H), 3.75 (s, 3H), 3.23 (d; 1H, J=13.69 Hz), 3.13 (d, 1H, J=13.69 Hz), 1.30 (s, 3H), 1.22 (t, 3H, J=7.43 Hz). MS [EI+] 331 (M+H)+, [EI−] 329 (M−H)+. Rf=0.14 in 25% ethyl acetate in hexanes.