Triethylamine → (4-Chloro-phenyl)-(2,5-dihydro-pyrrol-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

Pyrroline (4 mL, 54 mmol) was dissolved in THF (100 mL), Et3N (14 mL, 100 mmol) was added. The mixture was cooled to 0° C. 4-chloro-benzoyl chloride (7.6 mL, 60 mmol) was added very slowly at 0° C. Catalytic amount of DMAP was added too. Finally the reaction mixture was stirred at 0° C. to RT for overnight. The reaction mixture was diluted with ether and filtered to remove white solid of Et3N.HCl. Then evaporated to remove solvent and triturated with hexane/ether to give white solid 10.3 g with ratio of unsaturated/saturated about 3/1 by NMR. Then triturated with hexane/ether again to give 6.68 g white solid with ratio of unsaturated/saturated about 3.7/1 by NMR. 1H-NMR (300 MHz, CDCl3): δ 4.3 (4H, d), 5.80 (2H, d), 7.40 (4H, dd)

Provenance & Evidence