Chloroform → Ethyl 3-phenylthiopropionate

Participants

Reaction Steps

To a solution of 12.12 g (0.11 mol) of thiophenol, 10.01 g (0.10 mol) ethyl acrylate, 20 mL of HCCl3 at 0° C. in a 100-mL, round-bottom flask, 0.50 mL of triethylamine was added under N2. The ice bath was removed after the addition of triethylamine and the solution was allowed to stir at room temperature for 3 hours. The resulting solution was idluted with 150 mL of ether and washed with 10% NaOH, H2O, and saturated NaCl solution. The mixture was dried (Na2SO4, overnight) and the solvents were removed. Vacuum distillation gave 19.36 g (92.1%) of ethyl 3-(phenylthio)propionate as a clear, colorless liquid: bp 112°-115° C./0.2 mm [literature reports 117° C./2.5 mm; see K. Iwai, H. Kosugi, A. Miyazaki, and Huda, Synthetic Communications, 6, 357 (1976)]; IR (neat) 1740 cm-1 (C=O); 1H NMR (DCCl3) δ1.14 [t, 3H, CO2CH2CH3 ], 2.54 [t, 2H, CH2CO2CH2CH3 ], 3.10 [t, 2H, ArSCH2 ], 4.06 [q, 2H, CO2CH2CH3 ], 7.13-7.32 [m, 5H, ArH]; 13C NMR (DCCl3) ppm 13.6 [CO2CH2CH3 ], 28.3 [ArSCH2 ], 33.8 [CH2CO2CH2CH3 ], 60.0 [CO2CH2CH3 ], 125.8, 128.4, 129.3, 134.8, 170.9 [C=O]. Both hydrogen and carbon-13 NMR spectra shifts were measured from tetramethylsilane (TMS) standard on a Varian XL-300 spectrometer confirming the correct hydrogen distribution and carbon atom assignments. ##STR11##

Provenance & Evidence