Triethylamine → N-(2-Isobutoxy-3-methoxybenzyl)-N-methylacrylamide

Participants

Reaction Steps

To a solution of (2-isobutoxy-3-methoxybenzyl)methylamine (2.00 g, 8.96 mmol) in CH2Cl2 (80 mL) was added acryloyl chloride (0.85 mL, 9.8 mmol) drop-wise. After stirring for five minutes, triethylamine (1.37 mL, 9.86 mmol) was added. The solution was stirred for 6 hours. The solution was diluted with CH2Cl2 (30 mL) and then washed with H2O (3×100 mL) and brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (2.30 g, 92%) as a light yellow oil and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 7.06-6.93 (m, 2H), 6.85-6.62 (m, 1H), 6.57-6.53 (m, 1H), 6.17-6.13 (m, 1H), 5.73-5.63 (m, 1H), 4.64-4.58 (m, 2H), 3.79-3.78 (m, 3H), 3.69-3.66 (m, 2H), 2.95-2.87 (m, 3H), 2.01-1.98 (m, 1H), 0.99-0.97 (m, 6H).

Provenance & Evidence