Hydrochloric Acid → alpha-Methyl-2-pyridinemethanol

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Reaction Steps

To a solution of 110 g. of sodium borohydride in 1250 ml. of methanol at 0°C. is added 350 g. of 2-pyridyl methyl ketone in 300 ml. of methanol with stirring. After stirring for 4 hours at 0°-5°C., glacial acetic acid is cautiously added dropwise, followed by ice and concentrated hydrochloric acid. The acidic solution is made basic with aqueous sodium hydroxide and extracted with dichloromethane. The organic layer is dried over magnesium sulfate, concentrated and distilled to give 1-(2-pyridyl)ethanol.

Provenance & Evidence