Lithium Chloride → 1-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]ethanone

Participants

Reaction Conditions

Reaction Steps

Tributyl(1-ethoxyvinyl)stannane (95%, 1.39 mL, 3.88 mmol) was added to a mixture of 4-iodo-1-methyl-5-(4-methylphenyl)-1H-pyrazole (768 mg, 2.58 mmol), tetrakis(triphenylphosphine)palladium(0) (298 mg, 0.258 mmol) and lithium chloride (98%, 279 mg, 6.45 mmol) in N,N-dimethylformamide (20 mL), and the reaction was stirred at 90° C. for 18 hours. After cooling, the mixture was filtered through Celite, and concentrated in vacuo; silica gel chromatography (Gradient: 10% to 50% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 460 mg, 2.15 mmol, 83%. LCMS m/z 215.3 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.17 (s, 3H), 2.45 (br s, 3H), 3.69 (s, 3H), 7.28 (br AB quartet, JAB=8 Hz, ΔvAB=28 Hz, 4H), 7.99 (s, 1H).

Provenance & Evidence