Tributylamine → 3-Methyl-5-isopropylbenzofuran

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According to the method described by Xie et al. (Xie et al., (2004) Tetrahedron Lett. 45, 6235-6237) a mixture of allyl-2-iodo-4-isopropylphenyl ether (300 mg, 0.99 mmol), NBu3 (350 μL, 1.49 mmol), ammonium formate (65 mg, 1.03 mmol) and PdCl2 (10 mg, 0.06 mmol) in 1-butyl-3-methylimidazolium-tetrafluoroborate (1.5 mL) was heated at 60° C. for 2 days. A second portion of PdCl2 (24 mg) was added and the mixture was heated at 60° C. additional 5 h. The reaction mixture was extracted with Et2O. Evaporation of the solvent afforded 220 mg crude product, which was purified on silica giving the title compound in 30% yield (55 mg). 1H NMR (400 MHz, CDCl3) δ ppm 1.31 (d, J=6.90 Hz, 6 H) 2.24 (d, J=1.25 Hz, 3 H) 3.03 (spt, J=6.90 Hz, 1 H) 7.17 (dd, J=8.34, 1.94 Hz, 1 H) 7.34-7.39 (m, 3 H).

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