Triethylamine → (R)-N-methyl-N-[1-(3-methyl-benzofuran-2-yl)-ethyl]acrylamide

Participants

Reaction Steps

To an ice cold mixture of (R)-methyl-[1-(3-methyl-benzofuran-2-yl)-ethyl]amine (7.5 mL of a 0.46 M solution in DMF, 3.5 mmol) and Et3N (0.6 mL, 4.1 mmol) was added acryloyl chloride (0.3 mL, 3.8 mmol) drop-wise. The mixture was slowly warmed to room temperature and stirred overnight. The mixture was diluted with H2O and extracted with Et2O (3×). The combined organics were washed with H2O and satd NaCl, dried (Na2SO4) and concentrated. Purification by column chromatography (silica, gel, 7:3 hexanes/EtOAc) gave the title compound (630 mg, 75%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ7.50-7.47 (m, 1H), 7.44-7.41 (m, 1H), 7.30-7.20 (m, 2H), 6.81-6.52 (m, 1H), 6.40-6.25 (m, 2H), 5.74-5.70 (m, 1H), 2.99-2:90 (m, 3H), 2.23 (s, 3H), 1.69-1.58 (m, 3H).

Provenance & Evidence