2-(Trimethylsilylmethyl)allyl acetate → Methyl (+-)-trans-4-methylene-2-(3-fluorophenyl)cyclopentanoate

Beteiligte Stoffe

Reaktionsschritte

A mixture of methyl trans-3-fluorocinnamate (41.25 g, 229 mmol), tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mmol), 1,2-bis(diphenylphosphino)ethane (5.5 g, 13.7 mmol), and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (42.66 g, 229 mmol) in THF (300 mL) under nitrogen was heated to reflux for 6 h and then stirred at room temperature for 16 h. The reaction was diluted with hexane and filtered to remove the yellow precipitate. The volatiles were then removed in vacuo and the residue was purified by FC (3 to 5% ethyl acetate in hexanes) to afford the title compound (45 g).

Herkunft & Nachweise