Uses
Ethyl 2-((phenylsulfonyl)methyl)acrylate can be used in the synthesis of ethyl 2-{[(1s,2r,3r,5s)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methyl}acrylate that it is radical allylation of b-alkylcatecholboranes.
Synthesis
Ethyl 2-((phenylsulfonyl)methyl)acrylate is synthesized from ethyl 2-(bromomethyl)acrylate.
Step: To a solution of ethyl 2-(bromomethyl)acrylate (1.99 g, 10.4 mmol) in dry methanol (25 mL) was added sodium phenylsulfinate (2.50 g, 15.2 mmol). After 2.5 h of reflux the mixture was concentrated under reduced pressure, the obtained residue was dissolved in EtOAc and the mixture was washed with water, brine, dried with Na2SO4, filtered and the filtrate was evaporated and purified by chromatography (50% EtOAc/Petroleum ether) to give 35 as a viscous oil: Yield (1.94 g, 74%);
1H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 7.6 Hz, 2H), 7.64 (t, J = 7.6 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2H), 6.51 (s, 1H), 5.92(s, 1H), 4.17(s, 2H), 4.01(q, J = 7.2 Hz, 2H), 1.17(t, J = 7.2 Hz, 3H); 13C NMR (400 MHz, CDCl3) 164.73, 138.38, 133.86, 133.33, 129.11, 129.04, 128.77, 61.48, 57.52, 14.00.
