Potassium Carbonate → HCID 76538844, compound

Participants

Reaction Conditions

Reaction Steps

To a dry 1 L round bottom flask equipped with a magnetic stir bar, liquid addition funnel, thermometer, and nitrogen inlet were added potassium carbonate (33.2 g, 240 mmol) and pyrrolidine (136.5 g, 160 mL, 1.92 mol), and the resulting suspension was cooled to 0° C. in an ice bath. 3-(Methylthio)propionaldehyde (K) (50 g, 480 mmol) was added dropwise via the addition funnel at a rate which maintained the reaction temperature at 0-7° C. The resulting light yellow mixture was warmed to room temperature and stirred for 16 hours. The residual potassium carbonate was removed by filtration, the filter cake washed with Et2O, and the filtrate concentrated on the rotary evaporator to give the crude enamine as a viscous, light yellow oil. Fractional distillation (108-110° C. at 4 mm Hg) afforded 63.3 g (83.8%) of 1-[3-(methylthio)prop-1-enyl]pyrrolidine (L) as a colorless liquid. 1H NMR (CDCl3) δ 6.29 (d, 1H), 4.06 (dt, 1H), 3.16 (d, 2H), 3.03 (m, 4H), 2.04 (s, 3H), 1.85 (m, 4H). GC-MS (EI) m/z 157 (M+).

Provenance & Evidence