The information given below was retrieved and reworked from the publication: Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists by Andrea Behrenswerth, Nicole Volz, Jakob Toräng, Sonja Hinz, Stefan Bräse and Christa E. Müller. https://doi.org/10.1016/j.bmc.2009.02.027The reaction was conducted according to the general procedure: Under an atmosphere of argon, 0.602 mmol of substituted salicylaldehyde, 0.602 mmol of potassium carbonate, 1.51 mmol of a,b-unsaturated aldehyde and 0.602 mmol of 1,3-dimethylimidazolium dimethylphosphate were suspended in 2.00 ml of toluene. The reaction mixture was stirred at 100 °C for 24 hours, after which it was allowed to cool to room temperature. The reaction was quenched by addition of 10 ml of water. The product was extracted with 2 ´ 10 ml of EtOAc and 1 ´ 10 ml of dichloromethane. The combined organic phases were dried over magnesium sulfate and the solvent was removed under reduced pressure. The product was purified by flash column chromatography.Analysis of the target compound: 54.3 mg, 15% (Scale: 1.21 mmol). – Rf (n-Hex/EtOAc 20:1) = 0.10. – mp: 142–145°C. - 1H NMR (400 MHz, CDCl3): d = 3.84 (s, 3 H, OCH3), 4.00 (s, 2 H, CH2), 6.92–6.96 (m, 1 H, Har), 6.97–7.01 (m, 1 H, Har), 7.29–7.36 (m, 2 H, Har), 7.45 (d, 3J = 9.0 Hz, 1 H, Har), 7.52–7.54 (m, 1 H, Har), 7.58–7.62 (m, 1 H, Har), 7.86–7.91 (m, 2 H, Har), 8.02 (d, 3J = 8.3 Hz, 1 H, Har), 8.08 (s, 1 H, CH). - 13C NMR (100 MHz, CDCl3): d = 31.3 (s, CH2), 55.4 (p, OCH3), 110.6 (t, CarH), 113.6 (q, Car-CH), 116.8 (t, CarH), 120.8 (t, CarH), 121.4 (t, CarH), 125.7 (t, CarH), 126.0 (q, C-CH), 127.7 (q, Car-CH2), 127.8 (t, CarH), 127.9 (q, Car), 128.4 (t, CarH), 128.9 (t, CarH), 130.2 (q, Car), 131.3 (t, CarH), 131.6 (t, CH), 134.7 (t, CarH), 152.3 (q, Car-OCO), 157.6 (q, Car-OCH3), 161.9 (q, C=O). – IR (KBr): 1713 (s, n C=O) cm–1. - MS (EI): m/z (%) = 316 (100, M+), 304 (31), 285 (15, (M–CH3)+). - HR-EIMS (C10H8O2): calcd. 316.1099, found 316.1102.
