Methyl Acrylate → HCID 53811637, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-O-benzyl phenol (J. Med. Chem. (1992) 35:3483) (2.17 g; 8.25 mmol), methyl acrylate (0.83 g; 9.9 mmol), dichloropalladium(II)bis(triphenylphosphine) (150 mg) and triethylamine (2.51 g; 24.7 mmol) in 10 mL of DMF was heated in a sealed tube to 120° C. for 16 hrs. After cooling, the tube's contents were partitioned between ethyl acetate and water. Removal of the organic solvent and purification on silica gel (20% ethyl acetate/hexane) afforded 1.22 g (55%) of methyl 2-benzoxycinnamate, 1H NMR (CDCl3): δ 3.78 (s, 3H); 5.15 (s, 2H); 6.54 (d, 1H, J=16.2); 6.95 (m, 2); 7.33-7.41 (m, 6H); 7.52 (d, 1H, J=7.7).

Provenance & Evidence