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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TIBET

Tibet

Region in China

Tibet is a region on the Tibetan Plateau in China, Asia. It is the traditional homeland of the Tibetan people as well as some other ethnic groups such as Monpa, Qiang and Lhoba peoples and is now also ...Wikipedia

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