Methanol → [5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester

Participants

Reaction Steps

To a solution of 5-(2-benzyloxy-ethoxy)-2-nitro-benzoic acid (5.98 g, 18.85 mmol) in benzene (100 ml) and anhydrous tetrahydofuran (25 ml) was added triethyl amine (3.07 ml, 22 mmol) followed by diphenylphosphoryl azide (4.74 ml, 22 mmol). The reaction was stirred at room temp for 15 min, and then refluxed under nitrogen for 4 h. methanol (3 ml, 74.06 mmol) was added, and the reaction was refluxed for 18 h. The solvent was evaporated, and the oil chromatographed on silica gel eluting with 25% ethyl acetate/hexanes to give [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester (6.12 g, 94%) as an oil. Analysis calculated for C17H18N2O6 : C, 58.96; H, 5.24; N, 8.09. Found: C, 58.94; H, 5.11; N, 7.87

Provenance & Evidence