Triethylamine → N-(3-Methoxy-2-propoxybenzyl)-N-methylacrylamide

Participants

Reaction Steps

A solution of (3-methoxy-2-propoxybenzyl)methylamine (1.00 g, 4.78 mmol) in CH2Cl2 (40 mL) was treated with acryloyl chloride (0.42 mL, 5.2 mmol) followed by Et3N (0.74 mL, 5.3 mmol). After stirring for 1.5 h, the solution was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give the title compound (1.11 g, 88%) as a tan oil and as a mixture of amide rotamers: 1H NMR (300 MHz, CDCl3) δ 7.06-6.94 (m, 2H), 6.85-6.70 (m, 1H), 6.65-6.58 (m, 1H), 6.18-6.13 (m, 1H), 5.73-5.63 (m, 1H), 4.64-4.58 (m, 2H), 3.89-3.84 (m, 2H), 3.79-3.78 (m, 3H), 2.99-2.86 (m, 3H), 1.73-1.66 (m, 2H), 0.97 (t, J=7.4 Hz, 3H).

Provenance & Evidence