Phosphorus oxychloride → trans-6-(2,4-Dichlorphenoxymethyl)-2-[1-chloro-4-(2,4-dichlorophenyl)-2-butoxy]tetrahydropyran

Participants

Reaction Steps

2 Drops of phosphorus oxytrichloride were added to a solution of 388 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran and 418 mg of 1-chloro-4-(2,4-dichlorophenyl)-2-butanol in 8 ml of diethyl ether, and the mixture was allowed to react at room temperature for 2 days. At the the end of this time, 3 drops of triethylamine were added and the solvent was evaporated off. The residue was purified by column chromatography through silica gel eluted with a 50:5:1 by volume mixture of hexane, benzene and ethyl acetate, to give 185 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorphenoxymethyl)-2-[1-chloro-4-(2,4-dichlorophenyl)-2-butoxy]tetrahydropyran and 153 mg of the isomer of greater polarity.

Provenance & Evidence