Boron trifluoride etherate → 76369-00-1

Participants

Reaction Steps

At room temperature, to a solution of pyrrole-2-carboxylic acid (500 mg, 4,5 mmol) in anhydrous dichloromethane (5 mL) and anhydrous N,N-dimethylformamide (2.5 mL) was added anhydrous cyclohexane (20 mL). With vigorous stirring, to this clear solution was added (0.85 mL, 1.033 g, 4.73 mmol) of tert-butyl 2,2,2-trichloroacetimidate followed by dropwise addition of boron trifluoride diethyl etherate (170 mL). After stirring at room temperature for 2 hr, additional tert-butyl 2,2,2-trichloroacetimidate (0.85 mL, 1.033 g, 4.73 mmol) and boron trifluoride diethyl etherate (85 mL) were added to the reaction mixture. After stirring at room temperature for an additional 3 hr, additional tert-butyl 2,2,2-trichloroacetimidate (0.85 mL, 1.033 g, 4.73 mmol) and boron trifluoride diethyl etherate (85 mL) were added to the reaction mixture. After stirring at room temperature overnight, the reaction mixture was filtered through a pad of celite, and the residue was washed with ether. The solvent was removed from the filtrate by rotoevaportation and the crude product was purified by flash column chromatography on silica gel eluted with 3-6% ethyl acetate in hexane to give the title compound as a white solid (600 mg, 80% yield), homogeneous by TLC (1/1 hexane/Ethyl acetate).

Provenance & Evidence