Tetrabutylammonium Fluoride → HCID 178520859, compound

Participants

Reaction Steps

A 25 ml portion of THF solution containing 7.8 g of tetrabutylammonium fluoride and 24 g of Molecular Sieve 4A was stirred at room temperature for 12 hours in an atmosphere of argon. After cooling to 0° C., 20 ml of THF solution containing 300 mg of 3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]benzaldehyde and 1.7 g of diphenyl(2,2,2-trifluoroethyl)phosphine oxide was added dropwise thereto. This was stirred at room temperature for 5 hours. The reaction mixture was filtered, the filtrate was washed with water, dried with anhydrous sodium sulfate and concentrated, and then the thus formed residue was purified by a silica gel column chromatography to obtain 201 mg (57%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-{3-[(1Z)-3,3,3-trifluoroprop-1-en-1-yl]phenyl}propane-1,3-dione as a yellow powder from an ethyl acetate-hexane (1:3) eluate. FA: 463

Provenance & Evidence