Ethyl 2-(4-(benzyloxy)-2-formylphenoxy)-2-methylpropanoate → 2-(4-Hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl ester

反応式

[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][C:10]=1[CH:23]=[O:24])([CH3:7])[CH3:6])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:23][OH:24])([CH3:7])[CH3:6])[CH3:2]

参加物

実験手順

2-(4-Benzyloxy-2-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (185 g, 540 mmol) in ethanol (700 mL) was treated with 10% Pd/C (205 g) and hydrogen (60 psi) at 50° C. for 2 d. The mixture was filtered through Celite, washed with ethanol (1.5 L), and concentrated. The residue was recrystallized from EtOAc/hexanes to give the title compound (116 g). 1H NMR (400 MHz, CDCl3) δ 1.26 (t, 3H, J=7.3 Hz), 1.52 (s, 6H), 2.14 (s, 3H), 4.23 (q, 2H, J=7.3 Hz), 4.59 (brs, 2H), 6.61-6.68 (m, 2H), 6.77 (d, 1H, J=2.8 Hz).