Methoxymethyl-triphenylphosphonium chloride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine

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Reaction Steps

18.27 g of (methoxymethyl) triphenyl phosphonium chloride is suspended in 200 ml of anhydrous ether, 51.3 ml of phenyllithium (1.04 M) was dropped and the resulting mixture was stirred at a room temperature for 15 minutes. 145 ml of ether solution of 12.57 g of (4-chloro-3-difluoromethoxy-2-pyridyl)cyclopropylketone (X) was dropped to the mixture, which was stirred at a room temperature for 12 hours. The resulting residue was separated by filtering and washed with ether, and thereafter, the ether filtrate and ether used for washing were collected together and the collected solution was washed with water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.66 g of 2-(4-chloro-3-difluomethoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI).

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