Azobisisobutyronitrile → HCID 10979461, compound

Participants

Reaction Steps

A 25.37 g (0.11 mol) portion of (E)-ethyl 3-(1-ethoxycarbonylcyclopropyl)-2-butenoate was dissolved in 300 ml of carbon tetrachloride to which were subsequently added 23.9 g (0.13 mol) of N-bromosuccinimide and a catalytically effective amount of azobisisobutyronitrile, followed by 5 hours of reflux under sunlight. After completion of the reaction, the reaction solution was filtered and the resulting filtrate was concentrated. The thus obtained residue was dissolved in 250 ml of ethanol and mixed with 18.83 g (0.22 mol) of sodium bicarbonate. Thereto was added dropwise 15.84 ml (0.12 mol) of (S)-phenylethylamine at a room temperature. After completion of the dropwise addition, this was stirred for 30 minutes at room temperature and then heated for 4 hours under reflux. After completion of the reaction, the solvent was evaporated and the resulting residue was mixed with 500 ml of ethyl acetate, washed with water (500 ml×1), 1N hydrochloric acid (500 ml×2) and saturated brine (500 ml×2) in that order, and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was applied to a silica gel column chromatography to yield 13.1 g (39%) of the title compound as an oily substance from the eluate of n-hexane:ethyl acetate=1:1.

Provenance & Evidence