Water → 3-Methyl-N-phenylbut-2-enamide

Participants

Reaction Steps

In a 100 mL round bottom flask was placed NaH (1.93 g, 0.05 mol). After washing with dry hexane (2×10 mL dry THF (15 mL) was added), to this tan solid. Then, the resulting suspension was added to a solution of aniline (Compound 36, 4.89 mL, 0.054 mol) in dry THF (7 mL) at 0° C. After stirring for 30 min, 3,3-dimethylacryloyl chloride (Compound 35, 6.56 mL, 0.059 mol) was added dropwise to the above solution. The reaction mixture was stirred under N2 for overnight followed by a slow addition of water. The mixture was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with NH4Cl (sat.) and NaCl (sat.), dried over MgSO4 and concentrated to give the title compound as a tan solid (4.45 g, 51%). 1H NMR d 1.87 (s, 3H), 2.21 (s, 3H), 5.72 (s, 1H), 7.29-7.56 (m, 5H).

Provenance & Evidence