Dimethylformamide dimethyl acetal → 3-Dimethylamino-2-(2-trifluoromethyl-benzoyl)-acrylic acid ethyl ester

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A solution of 3-oxo-3-(2-trifluoromethyl-phenyl)-propionic acid ethyl ester, prepared following an analogous procedure to that outlined in Example 231, (3.14 g, 12.1 mmol, 1.0 equiv) and 1,1-dimethoxy-N,N-dimethylmethanamine (5.60 mL, 42.2 mmol, 3.5 equiv) in N,N-dimethylformamide was heated to reflux for 5 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed sequentially with water (4×) and saturated aqueous sodium chloride. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give 3.20 g (83%) of 3-dimethylamino-2-(2-trifluoromethyl-benzoyl)-acrylic acid ethyl ester as an orange waxy solid. 1H NMR (400 MHz, CDCl3) δ: 7.86 (s, 1H), 7.67-7.64 (m, 1H), 7.51-7.41 (m, 2H), 7.35 (d, 1H), 3.81 (q, 2H), 3.42-3.17 (m, 3H), 3.11-2.93 (m, 3H), 0.78-0.69 (t, 3H).

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