Imidazole → 3,5-Bis(methoxymethoxy)benzyl tert-butyldimethylsilyl ether

反応式

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.N1C=CN=C1.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1)[CH2:15][O:16][Si:26]([C:23]([CH3:25])([CH3:24])[CH3:22])([CH3:28])[CH3:27]

参加物

実験手順

To a solution of (3,5-bis-methoxymethoxy-phenyl)-methanol (220b) (290 g, 1.27 mol) and imidazole (129 g, 1.9 mol) in CH2Cl2 (1.5 L) was added TBSCl (286 g, 1.9 mol) at 5° C. in several portion was stirred at room temperature overnight. TLC (EtOAc/petroleum ether=1/2) showed that the reaction was complete. The mixture was filtered and the filtrate was washed with water, dried over Na2SO4 and concentrated under high vacuum to give the title compound (320 g, 97%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.68 (d, 2H), 6.57(t, 1H), 5.14 (s, 4H), 4.66 (s, 2H), 3.48 (s, 6H), 0.94 (s, 9H), 0.07 (s, 6H).