Aluminium lithium hydride → (6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanol

To a stirred solution of methyl 6-(2,2,2-trifluoroethoxy)picolinate (0.40 g, 1.69 mmol, Step-2) in THF (17 mL) is added slowly lithium aluminum hydride (0.096 g, 2.53 mmol) at 0° C. The resulting mixture is stirred at rt for 1 hour. The reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C. Then the mixture is diluted with DCM (50 mL) and celite is added to the mixture. After stirring at rt for 1 hour, the mixture is filtrated through a pad of celite, and the filtrate is concentrated in vacuo to give 0.32 g (92% yield) of the title compound as white solid. This material is used for the next reaction (Step-4) without further purification.

1. customThe reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C
2. additionThen the mixture is diluted with DCM (50 mL) and celite
3. additionis added to the mixture
4. stirringAfter stirring at rt for 1 hour
5. filtrationthe mixture is filtrated through a pad of celite
6. concentrationthe filtrate is concentrated in vacuo

ORD record

ord-422dd8f065d8477387161ddc3c0276a4

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187475B2