Potassium Carbonate → ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate

Participants

Reaction Steps

A mixture of K2CO3 (134 mg), ethyl(6-formyl-1-benzothiophen-3-yl)acetate (160 mg), ((2,6-dimethylpyridin-3-yl)methyl) (triphenyl)phosphonium chloride (323 mg) and DMF (5 mL) was stirred at room temperature for 3 d. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 179, 60 mg) and ethyl(6-((Z)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 180, 110 mg).

Provenance & Evidence