Ethyl pyridine-4-acetate → 4-Pyridineethanol

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.

1. custom, 3-neck round bottom flask which had been flushed with nitrogen
2. additionThe reaction mixture became yellow upon addition of the reducing agent
3. additionaddition
4. customthe mixture was quenched with 2.1 ml of water at 0° C.
5. filtrationfiltered through Celite
6. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-2c18fa354d1045c4aebcd1d3c345968c

Source dataset

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04968678