Pyridine → 5-(4-Fluorophenyl)-7-isopropyl-6-[4-(trifluoromethoxy)benzoyl]spiro[chromen-2,1'-cyclobutan]-4(3H)-one

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Reaction Conditions

Reaction Steps

68 mg (0.16 mmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are dissolved in 0.6 ml of abs. dichloromethane and cooled to −30° C. 9 μl (0.11 mmol) of pyridine are added, followed by the dropwise addition of 55 mg (0.11 mmol) of 5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro-[chromen-2,1′-cyclobutan]-4(3H)-one (Example 58A), dissolved in 0.4 ml of abs. dichloromethane. The mixture is slowly warmed to 0° C. and stirred at this temperature for 6 h. The mixture is diluted with ethyl acetate, 5 ml of 1 N aqueous sodium hydroxide solution are added and the mixture is then extracted twice with ethyl acetate. The combined organic phases are washed once with 1 N hydrochloric acid and twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product is dried under high vacuum and then reacted without further purification. This gives 54 mg (98% of theory) of the title compound.

Provenance & Evidence