Ethyl 6-chloronicotinate → (6-Chloropyridin-3-yl)methanol

To a solution of ethyl 6-chloronicotinate (25.8 g, 0.139 mol) in ethanol was added sodiumborohydride (10.5 g, 0.278 mol), followed by stirring under an atmosphere of nitrogen gas at room temperature. After 41 hours, the reaction mixture was concentrated and then the residue was diluted with a saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=4:1, 2:1, and 3:2), to give the title compound (11.7 g, 58%) as a pale yellow solid.

1. concentrationthe reaction mixture was concentrated
2. additionthe residue was diluted with a saturated aqueous ammonium chloride solution and ethyl acetate
3. washThe organic layer was washed with a saturated aqueous ammonium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated
6. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=4:1, 2:1, and 3:2)

ORD record

ord-c14b0c480a754feab16f1f7d3430561c

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07396836B2