Ammonium Chloride → 5-Chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran

Participants

Reaction Steps

528 mg (13.1 mmole) of sodium borohydride are added to a solution, cooled to 0°, of 3.3 g (13.1 mmole) of 5-chloro-6-(piperidin-1-yl)-benzofuran-3(2H)-one, according to Example 2, in 80 ml of methanol. The whole is subsequently stirred for a further 4 hours at 0°. The reaction mixture is diluted with water, adjusted to pH 6-7 with dilute ammonium chloride solution and extracted several times 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 methylene chloride as eluant (Rf =0.12) yields 5-chloro-3-hydroxy-6-(piperidin-1-yl)-2,3-dihydrobenzofuran in the form of an oil.

Provenance & Evidence