4-(2-Tert-butoxycarbonyl-vinyl)-3-ethyl-5-methyl-benzoic acid benzyl ester → 4-(2-Tert-butoxycarbonylethyl)-3-ethyl-5-methylbenzoic acid
反応式
C([O:8][C:9](=[O:28])[C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH:17]=[CH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:12]([CH2:26][CH3:27])[CH:11]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[C:22]([O:21][C:19]([CH2:18][CH2:17][C:13]1[C:14]([CH3:16])=[CH:15][C:10]([C:9]([OH:28])=[O:8])=[CH:11][C:12]=1[CH2:26][CH3:27])=[O:20])([CH3:23])([CH3:25])[CH3:24]参加物
4
実験手順
To a solution of 4-(2-tert-butoxycarbonyl-vinyl)-3-ethyl-5-methyl-benzoic acid benzyl ester (10.0 g, 26 mmol) in THF 100 mL), Pd/C (0.5 g, 20% Pd) is added under nitrogen. The mixture is stirred at rt for 48 h under 1 bar of H2. The catalyst is filtered off over a celite pad and the filtrate is concentrated to dryness to give 4-(2-tert-butoxycarbonyl-ethyl)-3-ethyl-5-methyl-benzoic acid (7.64 g) as a white solid; 1H NMR δ 1.29 (t, J=7.5 Hz, 3H), 1.49 (s, 9H), 2.36-2.41 (m, 2H), 2.74 (q, J=7.5 Hz, 2H), 2.99-3.05 (m, 2H), 7.77 (s, 1H), 7.80 (s, 1H).