Methyl Acrylate → HCID 10130436, compound

Participants

Reaction Conditions

Reaction Steps

To 4-bromoacetophenone (1 g, 5 mmol) in anhydrous DMF (30 mL) were added methyl acrylate (450 μL, 5 mmol), sodium bicarbonate (420 mg, 5 mmol) tetrabutylammonium bromide (1.61 g, 5 mmol) and palladium acetate (56 mg, 0.25 mmol) and the reaction mixture was heated at 130° C. for 2 h. The DMF was removed by concentration under reduced pressure, the crude was dissolved in EtOAc (100 mL) and washed with water (100 mL) then brine (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under vacuum to afford the crude product. This was purified by flash chromatography (1:1 heptane/EtOAc) to yield the desired product (784 mg, 77%). m/z=205 [M+H]+; 1H NMR (300 MHz, CDCl3) δ: 7.99 (2H, d, J=8.3 Hz), 7.73 (1H, d, J=16.2 Hz), 7.63 (2H, d, J=8.3 Hz), 6.55 (1H, d, J=16.0 Hz), 3.85 (3H, s), 2.64 (3H, s).

Provenance & Evidence