Diisopropylamine → HCID 59790305, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.122 mL (0.86 mmol) of diisopropylamine in THF at −78° C. was treated with 0.54 mL (0.54 mmol) of 1.6 M n-BuLI in hexanes, stirred at −78° C. for 0.5 h, treated dropwise with a solution of 0.22 gm (0.86 mmol) of difluoromethyldiphenylphosphine oxide in THF, stirred at −78° C. for 45 min, treated with a solution of 3-[3-(4-difluoromethoxyphenylethynyl)phenyl]propionaldehyde 0.17 gm (0.58 mmol) in THF, stirred at −78° C. for 4 h, warmed to room temperature, stirred at room temperature for 18 h and diluted with CH2Cl2. The organic phase was washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of this concentrate on silica gel with a gradient of hexanes to 10% EtOAc-hexanes yielded 1-(3-{[4-(difluoromethoxy)phenyl]ethynyl}-phenyl)-4,4-difluorobut-3-ene as an oil, 0.09 gm (52% yield); 1H NMR (400 MHz, CDCl3) δ: 2.29 (m, 2H), 2.66 (t, 2H, J=7.6 Hz), 4.13 (m, 1H), 6.50 (t, 1H, J=73.6 Hz), 7.07 (d, 2H, J=8.8 Hz), 7.13 (m, 1H), 7.26 (d, 1H, J=8.8 Hz), 7.34 (m, 2H), 7.49 (dt, 2H, J=2.1, 2.6, 8.3 Hz).

Provenance & Evidence