Sodium borohydride → HCID 23144439, compound

Temperature

0 °C

Ethyl 1-ethyl-6-oxo-1,6-dihydropyridine-2-carboxylate (2.25 g, 11.5 mmol) obtained in Step 1 was dissolved in ethanol (50 mL), and at 0° C., calcium chloride (2.56 g, 23.1 mmol) and sodium borohydride (2.18 g, 57.6 mmol) were added thereto, followed by stirring at 0° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of ammonium chloride was added to the resulting residue, followed by stirring at room temperature for 30 minutes. The reaction mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1) to afford 1-ethyl-6-(hydroxymethyl)-2-oxo-1,2-dihydropyridine (1.51 g, 76%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additiona saturated aqueous solution of ammonium chloride was added to the resulting residue
3. stirringby stirring at room temperature for 30 minutes
4. extractionThe reaction mixture was extracted with chloroform
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled away under reduced pressure
7. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1)

ORD record

ord-736226f5723141d4a83ac51c9a93e91a

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889718B2