反应详情

To a solution of 3-hydroxy-4-methyl-benzoic acid N′-[2-(4-chloro-phenyl)-acetyl]-hydrazide (0.91 g, 2.85 mmol) (from Example 39 supra) in acetonitrile (20 mL) was added diisopropylethylamine (3.0 mL, 17.1 mmol) and triphenylphosphine (1.50 g, 5.70 mmol). After stirring 5 minutes, hexachloroethane (1.01 g, 4.28 mmol) (Aldrich) was added and the mixture was allowed to stir for 2 days at room temperature. The solvent was evaporated. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (1×). The combined organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol. (Yield 0.68 g, 79%).

1. stirringto stir for 2 days at room temperature
2. customThe solvent was evaporated
3. customThe residue was partitioned between ethyl acetate and water
4. extractionThe aqueous phase was extracted with ethyl acetate (1×)
5. washThe combined organic phase was washed with water and brine
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography
9. washeluting with 20% ethyl acetate in hexanes to 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol