2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole → 2-[3-methoxy-4-(1H-tetrazol-1-ylmethyl)phenyl]-1,3-benzoxazole

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Reaction Steps

Utilizing the general procedure outlined for 2-[3-methoxy-4-(1H-1,2,3-triazol-1-ylmethyl)phenyl]-1,3-benzoxazole, reaction of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 1.0 mmol) and 1H-tetrazole (70 mg, 1.0 mmol) afforded 2-[3-methoxy-4-(2H-tetrazol-2-ylmethyl)phenyl]-1,3-benzoxazole and 2-[3-methoxy-4-(1H-tetrazol-1-ylmethyl)phenyl]-1,3-benzoxazole as colorless solids. 2-[3-methoxy-4-(2H-tetrazol-2-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 8.52 (s, 1H), 7.72–7.79 (m, 3H), 7.52–7.55 (m, 1H), 7.31–7.34 (m, 2H), 7.21 (d, 1H), 5.86 (s, 2H), 3.93 (s, 3H). MS (ESI) 308 (M+H). 2-[3-methoxy-4-(1H-tetrazol-1-ylmethyl)phenyl]-1,3-benzoxazole: 1H NMR (CDCl3, 300 MHz) δ 8.66 (s, 1H), 7.85 (d, 1H), 7.74–7.83 (m, 2), 7.55–7.59 (m, 1H), 7.41 (d, 1H), 7.34–7.40 (m, 2H), 5.61 (s, 2H), 3.98 (s, 3H). MS (ESI) 308 (M+H)+.

Provenance & Evidence