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

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Reaction Steps

30.78 g of (methoxymethyl) triphenyl phosphonium chloride is suspended in 300 ml of anhydrous ether and 102 ml of phenyllithium (0.88 M) was dropped thereto and the resulting mixture was stirred at a room temperature for 15 minutes. 210 ml of ether solution of 18.10 g of (4-chloro-3-methoxy-2-pyridyl)cyclopropylketone (X) was dropped thereto and 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 8.94 g of 2-(4-chloro-3-methoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI).

Provenance & Evidence