Diethyl [Chloro(cyano)methyl]phosphonate → 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3R)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate

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Reaction Steps

A solution of 0.27 g of potassium tert-butoxide in 2 ml of tetrahydrofuran was added dropwise to a mixture of 0.70 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3R)-2,2-dimethyl-3-formylcyclopropanecarboxylate, 0.42 g of diethyl(chlorocyanomethyl)phosphonate and 5 ml of anhydrous tetrahydrofuran with ice-cooling under a nitrogen atmosphere. After stirring with ice-cooling for 15 minutes, the reaction mixture was poured into a saturated saline solution and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was subject to silica gel column chromatography to obtain 0.03 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3R)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate represented by the formula (3):

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