Cyclopentane, methylene- → Methyl 4-(2-cyclopentylideneethoxy)benzoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of methyl 4-(allyloxy)benzoate 26.1 (3.00 g, 16.0 mmol) and methylenecyclopentane (1.9 g, 23.0 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in DCM (5.0 mL) was added Hoveyda-Grubbs reagent (0.39 g, 0.62 mmol), (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) at room temperature. The resulting reaction mixture was degassed three times and then stirred at 55° C. under nitrogen overnight. The reaction mixture was purified by CombiFlash® silica gel column chromatography (hexane/EtOAc 95/5) to give 26.2, (2.60 g, yield 68%). 1H NMR (500 MHz, CDCl3) δ ppm 7.82-7.93 (2H, m), 6.80-6.88 (2H, m), 5.44-5.56 (1H, m), 4.47 (2H, d, J=6.6 Hz), 3.80 (3H, s), 2.20-2.31 (4H, m), 1.50-1.71 (4H, m).

Herkunft & Nachweise