反应详情

A mixture of 3-methoxymethoxy-4-methyl-benzoic acid (1.96 g, 10 mmol) (from Example 50 supra), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.92 g, 10 mmol) (Aldrich) and 1-hydroxybenzotriazole hydrate (1.35 g, 10 mmol) (Aldrich) in N,N-dimethylformamide (25 mL) was stirred at room temperature for 30 minutes. Acetamide oxime (0.74 g, 10 mmol) (GFS Chemicals) was added and mixture heated at 140 C for 2 hours. After cooling, mixture was partitioned between ethyl acetate (2×) and saturated aqueous bicarbonate solution. Ethyl acetate solutions were combined and concentrated and residue purified by flash chromatography to give 5-(3-methoxymethoxy-4-methyl-phenyl)-3-methyl-[1,2,4]oxadiazole. (Yield 1.23 g, 52.5%).

1. temperaturemixture heated at 140 C for 2 hours
2. temperatureAfter cooling
3. custommixture was partitioned between ethyl acetate (2×) and saturated aqueous bicarbonate solution
4. concentrationconcentrated
5. customresidue purified by flash chromatography