Imidazole → tert-Butyldimethyl((4-nitrobenzyl)oxy)silane

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A solution of t-butyldimethylsilyl chloride (8.53 g, 56.3 mmol, 1.3 eq), imidazole (7.38 g, 108.3 mmol, 2.5 eq) and 4-nitro-benzyl alcohol (6.64 g, 43.3 mmol, 1 eq) in anhydrous DMF (25 mL) was stirred at room temperature under a N2 atmosphere for 72 h. The reaction mixture was diluted with H2O (500 mL) and extracted with Etoac (4×100 mL). The combined organic extracts were washed with H2O (100 mL), satd NaCl(aq) (100 mL), dried (MgSO4) and evaporated in vacuo. The residue was triturated with n-hexane and filtered. The filtrate was evaporated in vacuo to give the product as a yellow oil which crystallised (11.02 g, 95%). 1H NMR (CDCl3) δ 8.2 (d, J=8.25 Hz, 2H), 7.47 (d, J=8.02 Hz, 2H), 4.8 (s, 2H), 0.96 (s, 9H), 0.12 (s, 6H). IR (neat) 2955, 2930, 1605 and 1522 cm−1. HRMS m/z calcd for C13H22NO3 Si 268.1369 (M+H), found 268.1376

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