Methyl Acrylate → Methyl Cinnamate

Participants

Reaction Conditions

Reaction Steps

Compound 5 (30 mg, 2 μmol Pd), iodobenzene (0.20 g, 1 mmol), methyl acrylate (0.13 g, 1.5 mmol), sodium acetate (0.12 g, 1.5 mmol), and N,N-dimethylacetamide (3 mL) were sequentially added to a 15 mL septum-sealed test tube under protection of nitrogen. The reaction mixture was heated at 100° C. for 8 h. After it was cooled to the room temperature, 8 mL of anhydrous ether was added to precipitate compound 5. The mixture was centrifuged and the upper liquid layer was transferred via a syringe into a 20 mL round-bottom flask. Repeated the above precipitation procedure once. The combined liquid layer was concentrated under reduced pressure to give an oily residue. A saturated ammonium chloride solution (5 mL) was then added. The resulting mixture was extracted by ethyl acetate (10 mL×3), dried over anhydrous magnesium sulfate, filtrated, and concentrated to give a crude product. The crude product was further purified by column chromatography (silica gel, hexane/ethyl acetate=4/1) to give 0.16 g (99% yield) of trans-methyl cinnamate. Rf=0.53 (9:1 hexane:ethyl acetate), 1H NMR (300 MHz, CDCl3) δ 3.81 (s, 3H), 6.45 (d, J=15.6 Hz, 1H), 7.29–7.64 (m, 5H), 7.69 (d, J=15.6 Hz, 1H) ppm.

Provenance & Evidence