N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → (2z)-3-Fluoro-3-[4-(2-pyrimidinyl)phenyl]-2-propenal

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-(2-pyrimidinyl)phenyl]-2-propynal (210 mg, 1.01 mmol, prepared as described in Reference Example 300) and tetrabutylamonium dihydrogentrifluoride (50 wt % in 1,2-dichloroethane, 1.8 g, 3.0 mmol) was heated to 110° C. for 4 h. The cooled reaction mixture was diluted with ethyl acetate (30 mL), washed with aq. sat. NaHCO3 (30 mL) and brine (30 mL), and filtered through a plug of SiO2 (5 g). The SiO2 plug was rinsed with additional ethyl acetate (30 mL) and the combined filtrates were concentrated. Purification by chromatography (SiO2, 97:3 dichloromethane/ethyl acetate) provided 116 mg (51%) of the title compound as a colorless solid. MS 229 (M+H)+. Also isolated were (2Z)-3-chloro-3-[4-(2-pyrmidinyl)phenyl]-2-propenal (10 mg, 4%, MS 245, 247 (M+H)+) and recovered starting material (15 mg, 7%).

Provenance & Evidence