Water → HCID 18931461, compound

Participants

Reaction Steps

To a solution of 0.10 g (0.47 mmol) of N-(4-methylphenyl)-3-methoxyaniline (Compound 15) in 3.0 mL of tetrahydrofuran stirring at 0° C. under argon, were added 0.15 mL (0.11 g, 1.1 mmol) of triethylamine and then 0.19 g (1.6 mmol) of 3,3-dimethylacryloyl chloride. The reaction mixture was allowed to warm to room temperature over 30 minutes and then heated at 50° C. for 13 hours. The reaction mixture was cooled, water was added, and the mixture was extracted with diethyl ether (2x). The combined organic layers were then washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give an oil. The mixture was purified by flash chromatography (10% ethyl acetate in hexanes, 20% ethyl acetate in hexanes) to give the title compound as a yellow oil. PNMR (300 MHz, CDCl3) d 1.75 (3 H, s), 2.16 (3 H, s), 2.34 (3 H, s), 3.76 (3 H, s), 5.61 (1 H, s), 6.75-6.81 (2 H, m), 7.08 (2 H, d, J=8.5 Hz), 7.14 (2 H, d, J=8.5 Hz), 7.23 (1 H, t, J=7.8 Hz).

Provenance & Evidence