HCID 13671387, compound → Cyano(6-phenoxy-2-pyridinyl)methyl 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.95 g of 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylic acid and 1.70 g of cyano(6-phenoxy-2-pyridinyl)methyl tosylate in 30 ml of toluene was added 200 mg of tetrabutylammonium hydrogen sulfate. To this mixture was added in one portion 0.75 g of potassium carbonate dissolved in 10 ml of water. The reaction mixture turned from yellow to bright purple in 30 seconds. The reaction mixture was stirred vigorously and heated to 75° C. The purple color disappeared after 10 minutes. The reaction mixture was heated for four hours at 70° C. and then cooled to room temperature. The resulting mixture was washed with 100 ml of 5% potassium carbonate solution and extracted thrice with 50 ml portions of diethyl ether. The combined extract was stripped to give 440 mg of a crude oil. This crude product was chromatographed using 30% diethyl ether in hexane as eluent. The product was washed off the silica with ethyl acetate and the eluate was stripped to give 180 mg of the desired product as a yellow oil.

Provenance & Evidence