[C:1](=O)([O-])[O-].[Cs+].[Cs+].[N:7]1[NH:8][N:9]=[N:10][C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.IC>O1CCCC1.CN(C)C=O>[CH3:1][N:9]1[N:8]=[N:7][C:11]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:10]1A suspension of cesium carbonate (0.60 g, 1.83 mmol), 3-(2H-tetrazol-5-yl)-phenol (0.30 g, 1.85 mmol) (from Example 25 supra) in tetrahydrofuran-N,N-dimethylformamide (5:2, 17.5 mL) was heated at 70° C. for 3 hours. Iodomethane (0.29 g, 2.04 mmol) (Aldrich) was added. Heating was continued for 18 hours. 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 40% ethyl acetate in hexanes to give 3-(2-methyl-2H-tetrazol-5-yl)-phenol. (Yield 0.23 g, 70%).
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