Dimethylformamide → 4-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (Compound 301)(1 g, 0.186 mmol) in dimethylformamide under nitrogen atmosphere, were added cesium carbonate (4.5 g, 13.84 mmol), tetrakis(triphenylphosphine)palladium(0) (269 mg, 0.232 mmol) and 4-bromo-indan-1-one (1.35 g, 5.57 mmol) and the resultant reaction mixture was heated to 90° C. for 4 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-35% ethyl acetate in pet ether) afforded 4-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one as a solid.

Provenance & Evidence