1,2-Dimethoxyethane → HCID 22136239, compound

Participants

Reaction Steps

To a mixture of the crude methyl 3-(2-bromophenyl)propionate (1.59 g, ca 0.006 mol) and tetrakis(triphenylphosphine) palladium (0) (695 mg, 0.601 mmol) in 1,2-dimethoxyethane (45 mL) were added thiophene-2-boronic acid (2.304 g, 0.018 mol) and 1N aqueous NaHCO3 (15 mL). The resulting mixture was heated at reflux under nitrogen atmosphere for 66 hrs. The dark reaction mixture was then diluted with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4, filtered and then concentrated. The resulting crude product was purified by flash chromatography (5% EtOAc in hexane) to yield methyl 2-(2-thienyl)phenylpropionate as a light green oil.

Provenance & Evidence