Triethylamine → 1-(Thiophen-2-yl)prop-2-en-1-one

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Reaction Steps

12 g of 3-chloro-1-(thiophen-2-yl)propan-1-one) prepared in Example 1a are solubilized in ethyl ether (180 mL). Triethylamine (10.2 g; 100 mmoles) is added at room temperature. The mixture is left under stirring for 60 hours, then washed with a HCl 10% solution and extracted with ethyl ether (2×20 mL). The organic phase is anhydrified with sodium sulphate, filtered and the solvent removed under vacuum. 9.4 g of 1-(thiophen-2-yl)-prop-2-en-1-one are obtained (yellow oil, yield 99%). Rf=0.74 (ligroin/ethyl acetate 8/2 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.76 (m, 1H, ArH), 7.68 (m, 1H, ArH), 7.10 (m, 2H, ArH), 6.49 (m, 1H, CH2), 5.87 (m, 1H, CH2); 13C NMR (CDCl3) δ (ppm): 182.4, 144.6, 134.4, 132.5, 131.9, 129.4, 128.3; FT-IR (film) νmax: 3094.5, 1645.1, 1409.7, 1240.2, 850.4, 716 cm−1.

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