Methyl 2-(bromomethyl)-3-phenylacrylate → (E)-2-Formyloxymethyl-3-phenylacrylic acid methyl ester
Reaction equation
[CH:1]([O-:3])=[O:2].C([NH+](CC)CC)C.[CH3:11][O:12][C:13](=[O:24])/[C:14](/[CH2:22]Br)=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH3:11][O:12][C:13](=[O:24])/[C:14](/[CH2:22][O:3][CH:1]=[O:2])=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of triethylammonium formate (1.87 g) in acetonitrile (4 ml) was added (Z)-2-bromomethyl-3-phenylacrylic acid methyl ester (1.30 g) and the mixture heated at reflux for 2 hours. The reaction was cooled and extracted into diethyl ether (3×10 ml). The combined organics were dried (MgSO4) and concentrated under reduced pressure to afford the title compound as a crude oil.