Imidazole → 2-((Tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-methyl-5-nitropyridin-2-yl)methanol (1.2 g, 7.1 mmol) in 5 mL of CH2Cl2, were added tert-butylchlorodiphenylsilane (2.0 g, 7.1 mmol) and imidazole (0.049 g, 0.71 mmol) at an ambient temperature. The reaction was stirred at 25° C. for 2 hrs. The reaction was poured into H2O, extracted with ethyl acetate, and dried over MgSO4. The ethyl acetate was concentrated under vacuum and purified over SiO2 to afford the desired compound 2-((tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine in 90% (2.6 g). 1HNMR (CDCl3, 400 MHz) δ 1.12 (s, 9H), 2.78 (s, 3H), 4.85 (s, 2H), 7.21 (s, 1H), 7.24˜7.89 (m, 10H), 9.15 (s, 1H).

Provenance & Evidence