Pyridine → HCID 86739182, compound

Participants

Reaction Steps

Under a dry nitrogen atmosphere, a stirred solution of 1.2 g (0.006 mol) of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid in 40 mL of toluene was heated to 80° C.±5° C. To this solution was added a solution of 0.7 g (0.006 mol) of oxalyl chloride in 5 mL of toluene. Upon complete addition, the reaction mixture was heated at 82° C.±5° C. for 60 hours. The reaction mixture was cooled to ambient temperature, and 0.9 g (0.011 mol) of pyridine was added. The reaction mixture was stirred for two hours, then warmed to 70° and 1.4 g (0.006 mol) of 3-(2-bromo-5-furanyl)phenylmethanol in 10 mL of toluene was added. Upon complete addition, the reaction mixture was stirred at 70° C.±5° C. for 21.5 hours. The reaction mixture was transferred to a separatory funnel, 200 mL of toluene washings were added, and the mixture was washed with 100 mL of an aqueous 2 N hydrochloric acid solution, 100 mL of a saturated aqueous solution of sodium chloride, 100 mL of an aqueous 2 N solution of sodium hydroxide, and finally 100 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to medium pressure liquid chromatography using hexane:ethyl acetate (46:1). The appropriate fractions were combined and concentrated to give a crystalline solid. The solid was recrystallized from methanol, then from hexane to give 0.9 g of [3-(5-bromofuranyl)phenyl]methyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, m.p. 76.5°-77° C.

Provenance & Evidence