3-Pyridinecarboxaldehyde → 1-(Pyridin-3-yl)propan-1-ol

A solution of nicotinaldehyde (0.200 mL, 0.12 mmol) in THF (2.0 mL) was slowly added to ethylmagnesium bromide (1.0 mol/L solution in THF, 3.18 mL, 3.18 mmol) at 0° C. The mixture was stirred at the same temperature for 1 hour and a saturated aqueous ammonium chloride solution was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give Compound A19 (194 mg, 67% yield).

1. extractionExtraction with ethyl acetate
2. washwashing with saturated brine
3. dry with materialdrying over anhydrous sodium sulfate
4. filtrationAfter filtration
5. customthe solvent in the filtrate was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)
7. customto give Compound A19 (194 mg, 67% yield)

ORD record

ord-ce8a387a4474404492373b2f4e21066e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150569B2