Ethyl Acetate → HCID 86656478, compound

Participants

Reaction Steps

Solid Pd(PPh3)4 (10 mg, 8.69 pmol) was added to a stirred solution of the mono-triflate 9 (230 mg, 0.22 mmol) in toluene (3 mL), EtOH (10 mL), with 4-methoxyphenyl boronic acid (43 mg, 0.28 mmol), Na2CO3 (37 mg, 0.35 mmol), in H2O (1.5 mL) at room temperature. The reaction mixture was allowed to stir under a nitrogen atmosphere for 20 h, at which point the reaction was deemed complete as judged by LC/MS and TLC (EtOAc). The solvent was removed by rotary evaporation under reduced pressure in vacuo and the resulting residue partitioned between EtOAc (75 mL) and H2O (75 mL). The aqueous phase was extracted with EtOAc (3×30 mL) and the combined organic layers washed with H2O (30 mL), brine (40 mL), dried (MgSO4), filtered and evaporated to provide the crude product. The crude product was purified by flash chromatography (60% Hexane: 40% EtOAc→80% EtOAc: 20% Hexane) to provide the pure dimer as an orange foam. Removal of the excess eluent under reduced pressure afforded the desired product 10 (434 mg) in 74% yield.

Provenance & Evidence