Sodium borohydride → HCID 12838411, compound

Participants

Reaction Steps

243 g of 1-(m-methoxyphenyl)-2-oxo-cyclohexane-1-acetonitrile are dissolved in 2.5 liters of ethanol, whereupon a total of 25 g of sodium borohydride is added portionwise while stirring. The temperature rises to about 45° C. After 1 hour, 1-(m-methoxyphenyl)-2-oxo-cyclohexane-1-acetonitrile can no longer be detected by thin-layer chromatography. After distillation of the solvent, the residue is treated with 500 ml of ice water and extracted twice with 1.5 liters of ether each time. The combined extracts are washed once in succession with 0.5 liter of water, 0.5 liter of 1 N hydrochloric acid and 0.5 liter of water, dried over magnesium sulfate, and the solvent is removed by distillation, whereby there are obtained 240 g of 1-(m-methoxyphenyl)-2-hydroxy-cyclohexane-1-acetonitrile in the form of a colorless, viscous oil which is dissolved without purification in 2 liters of pyridine and treated with 130 ml of phosphorus oxychloride. The mixture is boiled at reflux for 3 hours and subsequently evaporated in a water-jet vacuum. The residue is treated with water while cooling with ice and extracted twice with 1.5 liters of ether each time, whereupon the ethereal phases are combined, washed once in succession with 0.5 liter of water and 0.5 liter of 1 N hydrochloric acid and subsequently twice with water, dried over magnesium sulfate and evaporated. The brown oil obtained is purified on a 10-fold amount of silica gel. After elution of the impurities with about 10 liters of ether/petroleum ether (1:9), 1-(m-methoxyphenyl)-2-cyclohexene-1-acetonitrile is eluted with about 10 liters of ether/petroleum ether (1:3). The fractions which are uniform in accordance with thin-layer chromatography are combined, and the solvent is removed by distillation and the product remains behind as a light yellow oil.

Provenance & Evidence