2-(Bromomethyl)acrylic acid ethyl ester → HCID 10492188, compound

Participants

Reaction Steps

To a solution of 7a (0.60 g, 3 mmol) in dry tetrahydrofuran (60 ml) were added activated zinc powder (0.26 g, 3.9 mmol), hydroquinone (6 mg), and ethyl 2-(bromomethyl)acrylate (0.78 g, 4 mmol). The mixture was refluxed under nitrogen atmosphere for 6 h (monitored by TLC). After cooling, it was poured into an ice-cold 5% HCl solution (300 ml), neutralized with 1.0N NaHCO3, and extracted with CH2Cl2 (60 ml×3). The dichloromethane extracts were combined and washed with water, dried over Na2SO4, and then evaporated to give a residual oil which was purified by column chromatography on silica gel using CH2Cl2 as the eluent to afford the title compound (0.66 g, 82%). UV λmax (log ε): 250 (4.69) (0.1N HCl in MeOH), 237 (4.60) (MeOH), 238 (4.64) (0.1N NaOH in MeOH); 1H-NMR (CDCl3): δ1.61 (s, 3H, 2'-CH3), 2.84 (dt, 1H, 3'-H), 3.48 (dt, 1H, 3'-H), 4.25 (d, 1H, OCH), 4.32 (d, 1H, OCH), 5.66 (t 1H, vinylic H), 6.26 (t, 1H, vinylic H), 7.13-8.91 (m, 6H, Ar--H). Anal. Calcd for C16H15NO3.1/8H2O: C, 70.77; H, 5.65; N, 5.16. Found: C, 70.80; H, 5.75; N, 5.08.

Provenance & Evidence