Pyridine → HCID 21547127, compound

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Reaction Steps

20.0 Gm (0.0734 mol) of 6-(2'-fluoro-4-biphenylyl)-2-hexanol were dissolved in a mixture consisting of 110 ml of anhydrous dimethyl sulfoxide, 110 ml of absolute benzene, 5.9 ml (0.0732 mol) of pyridine and 2.95 ml (0.0397 mol) of trifluoroacetic acid. 45.5 Gm (0.22 mol) of N,N'-dicyclohexylcarbodiimide were added to the solution, and the mixture was stirred at room temperature for 14 hours. Then, the mixture was diluted with 2 liters of dry ether, a solution of 27.7 gm (0.22 mol) of oxalic acid dihydrate in 180 ml of methanol was added dropwise while stirring, and 2 liters of water were added after the gas evolution, lasting about 30 minutes, was compete. The insoluble N,N' -dicyclohexyl-urea was filtered off, and the aqueous and organic layers were separated. The organic layer was washed twice with aqueous 5% sodium bicarbonate solution and once with water, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silicagel, using benzene as the eluant, and was subsequently recrystallized three times from petroleum ether. Yield: 7.0 gm (35% of theory) of colorless crystals, m.p. 37°-38°C.

Provenance & Evidence