Sodium borohydride → 1-(3-Chloropyridin-2-yl)ethanol

To a stirred solution of 0.20 g (1.2 mmol) of 1-(3-chloropyridin-2-yl)ethanone in 5 mL of methanol was added 0.072 g (1.9 mmol) of sodium borohydride and the resulting solution was stirred with gradual warming to ambient temperature over 1 h. The reaction mixture was carefully quenched with water and then all volatiles were removed in vacuo. The remaining aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a colorless gum (0.15 g, 75% yield). LC-MS: m/z (ES) 158.2 (MH)+.

1. customThe reaction mixture was carefully quenched with water
2. customall volatiles were removed in vacuo
3. extractionThe remaining aqueous phase was extracted with ethyl acetate
4. washthe combined organic layers were washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated to dryness in vacuo
8. customThe residue was purified by silica gel chromatography
9. washeluting with a 0-100% ethyl acetate in hexanes gradient

ORD record

ord-1737c5f1f131490a9e09194768fad16d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354403B2