Tetrahydrofuran → 4-(2-Hydroxytetrazol-1-yl)-1-benzyloxybenzene

Participants

Reaction Steps

To a 100 mL recovery flask was added THF (20 mL) and a stirbar. The flask was cooled to 0° C. whereupon AlCl3 (751 mg, 5.63 mmol, 1.1 eq.) was added. The solution was stirred for 15 min whereupon NaN3 (1.00 g, 15.4 mmol, 3.0 eq.) and 4-benzyloxy-phenylisocyanate 51 (1.15 g, 5.12 mmol, 1.0 eq.) was added. The reaction mixture was refluxed overnight. The reaction mixture was quenched with 1N HCl (50 mL) and diluted with EtOAc (100 mL). The organic phases were washed with brine and the combined aqueous phases were extracted with EtOAc (3×50 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give an off-white solid that was used in subsequent reactions without further purification. (515 mg, 37%)

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