Hexachloroethane → 5-(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)-2-methylphenol

Participants

Reaction Steps

To a solution of 3-hydroxy-4-methyl-benzoic acid N′-(4-chloro-benzoyl)-hydrazide (1.28 g, 4.20 mmol) (from Example 44 supra) in acetonitrile (20 mL) was added diisopropylethylamine (4.4 mL, 25.2 mmol) and triphenylphosphine (2.21 g, 8.40 mmol). After stirring 5 minutes, hexachloroethane (1.49 g, 6.30 mmol) (Aldrich) was added and the mixture was allowed to stir for 1 day 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 washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography eluting with 0-60% ethyl acetate in hexanes to give 5-[5-(4-chloro-phenyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol. (Yield 0.34 g, 28%).

Provenance & Evidence