Potassium Carbonate → Methyl 2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A dry round bottom flask containing 8.7 (1.13 g, 3.31 mmol), 3-ethoxyphenylboronic acid (available from Aldrich) (1.10 g, 6.63 mmol), tetrakis(triphenylphosphine)palladium (0.39 g, 0.340 mmol), and potassium carbonate (1.41 g, 10.20 mmol) was evacuated and backfilled three times with argon. Dry DMF (10.000 mL) was then added via syringe under argon. The mixture was then heated at 80° C. and monitored with TLC. After 20 hours, the reaction was cooled to room temperature and diluted with water. The mixture was extracted three times with EtOAc and then concentrated under reduced pressure. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-25% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 41.1 as a colorless oil (0.87, 84%). MS ESI (pos.) m/e: 313.1 (M+H)+.

Provenance & Evidence