[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[I-].[K+].[N:13]1[NH:14][N:15]=[N:16][C:17]=1[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:14]2[N:15]=[N:16][C:17]([C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)=[N:13]2)=[CH:5][CH:4]=1A suspension of 4-methoxybenzylchloride (0.26 mL, 1.94 mmol) (Aldrich), potassium iodide (0.31 g, 1.85 mmol) (Aldrich), 3-(2H-tetrazol-5-yl)-phenol (0.3 g, 1.85 mmol) (from Example 25 supra), potassium carbonate (0.38 g, 2.78 mmol) and 18-crown-6 (24.0 mg, 0.09 mmol) (Aldrich) in N,N-dimethylformamide (15 mL) was heated at 65° C. for 1 day. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 5-40% ethyl acetate in hexanes to give 3-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-phenol. (Yield 0.38 g, 73%).
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