Ethyl pyridine-4-acetate → 4-Pyridineethanol

Participants

Reaction Steps

Fifteen grams (0.091 mol) of 4-pyridineacetic acid ethyl ester was dissolved in 180 ml of dry THF. The solution was transferred to a 1 l., 3-neck round bottom flask which had been flushed with nitrogen. To the mixture was added dropwise 55 ml of 1.0 M lithium aluminum hydride (0.055 mol) at approximately 0° C. The reaction mixture became yellow upon addition of the reducing agent. Following addition, the mixture was quenched with 2.1 ml of water at 0° C. followed by 2.1 ml of 15% by volume of sodium hydroxide and 6.3 ml of water. The mixture was allowed to stir at room temperature for approximately 4 hours and filtered through Celite. The filtrate was concentrated under vacuum to provide 6.38 g of 4-pyridineethanol. This material was used directly in the following reaction.

Provenance & Evidence