Acetic Acid → Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',3',5',6'-tetramethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate

Participants

Reaction Steps

To a solution of 4′-(2-ethoxyethoxy)-2′,3′,5′,6′-tetramethylbiphenyl-3-carbaldehyde (0.300 g, 0.99 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.194 g, 0.99 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.158 mL, 2.76 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.585 g, 2.76 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.400 g, yield 84%) as a colorless oil.

Provenance & Evidence