Sample Experimental Section
Last Updated on Saturday, March 08, 2008.
(2E,11E)-Diethyl 7-(1,3-dioxoisoindolin-2-yl)trideca-2,11-dienedioate
To a stirring solution of 2-(undeca-1,10-dien-6-yl)isoindoline-1,3-dione (0.168 mmol, 50 mg, 1 eq) in dichloromethane was added ethyl acrylate (1.02 mmol, 0.11 mL, 6 eq) followed by Hoveyda-Grubbs 2nd generation catalyst (0.0042 mmol, 3 mg, 2.5 mol%) as a solid. The solution was stirred for 96 h at room temperature, monitoring by TLC, after which time another portion of catalyst (0.0042 mmol, 3 mg, 2.5 mol%) was added. The reaction mixture was stirred at room temperature for a further 24 h, at which point it was concentrated and subjected to purification by column chromatography (over SiO2 eluting with 6:1 hexane / ethyl acetate) yielding the product (0.149 mmol, 66 mg, 89%) as a clear yellow oil: Rf 0.6 (SiO2, 2:1 hexane / ethyl acetate); MS (EI/CI): m/z [m+Na]+ 464.2 (100%) HRMS calculated for C25H31NNaO6 (M+Na) 464.2044, found 464.2069; δH (270 MHz; CDCl3) 7.79 - 7.84 (2H, m) 7.69 - 7.74 (2H, m) 6.84 (2H, dd, J 15.70 and 7.02) 5.79 (2H, dt, J 15.70 and 1.45) 4.14 (4H, q, J 7.16) 2.03 - 2.25 (5H, m) 1.61 - 1.79 (4H, m) 1.33 - 1.46 (4H, m) 1.19 - 1.30 (6H, m); δC (270 MHz, CDCl3) 166.7, 148.4, 134.1, 131.7, 123.4, 121.8, 60.3, 51.5, 32.0, 31.8, 25.1, 14.3; IR (thin film, ν/cm-1) 1706.