Sodium borohydride → [2-(Trifluoromethyl)pyridin-3-yl]methanol

To a suspension of sodium borohydride (0.24 g, 6.32 mmol) in anhydrous THF (40 mL) at 0° C. was added dropwise a solution of methyl 2-(trifluoromethyl)pyridine-3-carboxylate (650 mg, 3.16 mmol) in THF (50 mL). After stirring for 1 hour, the reaction mixture was slowly quenched with 15% NaOH and then diluted with water. Ethyl acetate was added, the reaction mixture was stirred for 10 minutes, and the precipitated white solid was filtered off. The solid was washed with ethyl acetate (3×100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to provide [2-(trifluoromethyl)pyridin-3-yl]methanol as a thick oil (0.505 g, 90% yield), which was used for the next step without any further purification; M+177.1.

1. customthe reaction mixture was slowly quenched with 15% NaOH
2. additiondiluted with water
3. additionEthyl acetate was added
4. stirringthe reaction mixture was stirred for 10 minutes
5. filtrationthe precipitated white solid was filtered off
6. washThe solid was washed with ethyl acetate (3×100 mL)
7. customThe organic layer was separated
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. customThe filtrate was evaporated

ORD record

ord-8e4386a4c0c648ab84ffcbcd67bed2dd

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315521B2