Imidazole → (4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

Participants

Reaction Steps

To a stirred solution of 4-nitrobenzyl alcohol (1.00 g, 6.50 mmol) and imidazole (0.97 g, 14.10 mmol) in DMF (10.0 mL), t-butyl-diphenyl-chlorosilane (1.98 g, 1.87 mL, 7.20 mmol) was added over 10 min under nitrogen at room temperature. The reaction mixture was stirred for an additional 5 h, diluted with 75 mL Et2O, washed with H2O (5 times, 15 mL), dried (MgSO4) and evaporated under vacuum. An oil which crystallised on standing, resulted; yield: 2.54 g. After recrystallisation from EtOH 70%, 2.36 g (93%) of a white soiid is obtained mp 80-81° C. νmax /cm-1 (film): 2931. 2857 (CH2, asym., sym.), 1521. 1345 (NO2); 1H-NMR, δH : 1.06(9H, s, t-Bu), 4.92 (2H, s, CH2), 7.42-7.46 (5H, m, Ph), 7.63-7.65 (7H, m, Ph+Harom2+6), 8.23, (2H, d, J=8.23 Hz, Harom3+5); MS, (EI), (391.54); m/z: 334 (M-t-Bu, 100), 288 (M-t-Bu-NO2, 10), 256 (M-t-Bu-Ph, 20), 199 (Ph2SiOH+, 100); C23H25NO3Si.

Provenance & Evidence