[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.C(OCC)C>[CH2:15]([O:14][CH2:13][N:2]1[N:3]=[N:4][CH:5]=[N:1]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([O:14][CH2:13][N:1]1[CH:5]=[N:4][NH:3][NH:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1A suspension of 1-H-tetrazole (2.0 g, 28.5 mmol) and potassium carbonate (5.9 g, 42.7 mmol) in DMF (30 mL) was treated with benzyl chloromethyl ether (5.36 g, 34.2 mmol), and the reaction mixture was stirred for 4 hours. After this time, the reaction mixture was analyzed by LC/MS, which indicated that the reaction was not complete. As a result, the reaction was treated with benzyl chloromethyl ether (0.5 g, 3.19 mmol) and stirred for about 16 additional hours. At the conclusion of this period, the mixture was filtered, and the filtrate was concentrated in vacuo to yield a residue. The residue was diluted with diethyl ether (200 mL), washed 5× with water (50 mL), once with brine, dried over sodium sulfate, and then concentrated in vacuo. The resulting residue was purified over a 6×20 mm silica gel column, eluting with 20% then 30% ethyl acetate/hexanes to yield 2-(benzyloxymethyl)-2H-tetrazole (2.39 g, 44% yield) and 1-(benzyloxymethyl)-2H-tetrazole (2.56 g, 47% yield).
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