Potassium Iodide → HCID 59649708, compound

Participants

Reaction Conditions

Reaction Steps

A 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%).

Provenance & Evidence