Ammonium Chloride → N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamide

Participants

Reaction Steps

An amount (61 mg) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in t-butyl methyl ether (2 ml); to the solution, 1.69 M n-butyllithium (0.148 ml) was added at −70° C. under a nitrogen atmosphere and the mixture was stirred for 10 minutes. To the reaction mixture, 2-cyanoethyl isocyanate (28 mg) was added and the resulting mixture was stirred at −70° C. for 10 minutes. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, followed by extraction with hexane/ethyl acetate (1/1); the resulting organic layers were washed with a 1 N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried with anhydrous sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=3/2) to give the titled compound (45 mg) as a colorless oil.

Provenance & Evidence