Methanol → Methyl pyrazinoate

To methanol (8.0 mL), thionyl chloride (2.08 mL) was added dropwise under a nitrogen atmosphere at −10° C. and the mixture was stirred at the same temperature for 30 minutes. To this, 2-pyrazinecarboxylic acid (1.00 g, 8.06 mmol) was added at the same temperature and the mixture was stirred at room temperature for 72 hours. The reaction mixture was concentrated, a saturated aqueous sodium bicarbonate solution was added to the residue, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol 19/1) to give methyl 2-pyrazinecarboxylate (969 mg, yield: 87%).

1. stirringthe mixture was stirred at room temperature for 72 hours
2. concentrationThe reaction mixture was concentrated
3. additiona saturated aqueous sodium bicarbonate solution was added to the residue, and extraction with ethyl acetate
4. washby washing with brine
5. dry with materialdrying over anhydrous sodium sulfate
6. customThe solvent was evaporated off under reduced pressure
7. customthe residue was purified by silica gel column chromatography (chloroform/methanol 19/1)

ORD record

ord-0fb30a23b46545a985a718535e5dd971

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2