Pyridine → HCID 86738497, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2.0 grams (0.011 mole) of 2-methyl-3-(pyrrol-1-yl)phenylmethanol (prepared in Example 2), and 0.9 gram (0.011 mole) of pyridine in 30 ml of toluene was warmed to 50° C. Under a dry-nitrogen atmosphere 2.8 grams (0.011 mole) of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride in 2 ml of toluene was added in one portion. The addition caused an exothermic reaction which raised the reaction mixture temperature from 50° C. to 55° C. Upon complete addition the reaction mixture was heated to 60° C. where it was stirred for 2.5 hours. The reaction mixture was cooled and poured into a separatory funnel with 300 ml of heptane. The resultant organic layer was washed with 100 ml of an aqueous solution of 2 N hydrochloric acid then with 200 ml of an aqueous solution of 2 N sodium hydroxide. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was purified by distillation using a Kugelrohr distilling system to give 3.8 grams of [2-methyl-3-(pyrrol-1-yl)phenyl]methyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate, bp 135° C./0.04 mm.

Provenance & Evidence