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Friday 24 June 2016

5-methylene-2-phenyl-4,5-dihydrooxazole






5-methylene-2-phenyl-4,5-dihydrooxazole 2:

 in a dried, round-bottomed Schlenk-flask, 3.18 g (20 mmol) of propargyl amide 1 were dissolved in 60 mL of dry DCM. Then, 62 mg (0.5 mol %) of IPrAuCl and 39 mg (0.5 mol %) of AgNTf2 were added under an atmosphere of nitrogen. The reaction mixture was stirred for 24 h at room temperature. The solvent was evaporated, a small amount of PE/EA was added, and the raw product was purified by column chromatography on silica (PE/EA 15:1) to yield 2.94 g (18.4 mmol, 92%) of oxazoline 2 as a light yellow oil. Rf (PE/EA 5:1 = 0.66). 

1H NMR (300 MHz, CDCl3) δ = 4.34 (q, J = 2.7 Hz, 1H), 4.63 (t,J = 2.9 Hz, 2H), 4.80 (q, J = 3.0 Hz, 1H), 7.55–7.35 (m, 3H), 8.01–7.90 (m, 2H). GC-MS (EI) m/z = 159.0 (M), 144.0 (M – CH2 – H), 131.1, 117.0, 103.0, 89.0, 77.0 (Ph).
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