Potassium Hydroxide → HCID 18470773, compound

Participants

Reaction Steps

To a stirred solution of 3-acetyl-5-bromo-2,4-dimethyl-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole (309 mg, 0.85 mmol) in toluene (5 mL) was added diethyl(4-pyridyl)borane [prepared according to the method of M. Terashima et al., Heterocycles, 1984, 22, 2471] (250 mg, 1.70 mmol), potassium hydroxide (85% purity, 168 mg, 2.55 mmol), and tetrakis(triphenylphosphine)palladium (0) (100 mg, 0.085 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 3 hours. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:1) to give the title product (105 mg, 36% yield).

Provenance & Evidence