5-Chloro-3-hydroxy-3-methyl-6-(piperidin-1-yl)-2,3-dihydrobenzofuran → 5-Chloro-3-methyl-6-(piperidin-1-yl)-benzofuran

Participants

Reaction Steps

A solution of 1.4 g (5.2 mmole) of 5-chloro-3-hydroxy-3-methyl-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in 20 ml of acetic acid/5N hydrochloric acid 1:1 is maintained at 85° for one hour. The reaction mixture is concentrated in a vacuum rotary evaporator, water is added to the residue and the whole is adjusted to pH 7 with saturated sodium carbonate solution and extracted with methylene chloride. The organic phases are washed with water, combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Chromatography over silica gel using chloroform as eluant yields 5-chloro-3-methyl-6-(piperidin-1-yl)-benzofuran which, after recrystallisation from petroleum ether, melts at 82°-84°.

Provenance & Evidence