Ethyl formate → Methyl 2-formyl-3-(pyridin-3-yl)propanoate
Reaktionsgleichung
[Na].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.[CH:14](OCC)=[O:15]>CCOCC.O>[CH:14]([CH:9]([CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:15]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a suspension of 2.1 g (90.8 mmol) of sodium in 55 mL of anhydrous Et2O is added dropwise, at 0° C. under argon, a mixture of 15 g (90.8 mmol) of methyl 3-(pyridin-3-yl)propanoate and 7.3 mL (57.41 mmol) of ethyl formate. The medium is then stirred for 12 hours at room temperature, taken up in 200 mL of water and extracted with 100 mL of Et2O. The aqueous phase is acidified to pH 5 and then extracted with 2×300 mL of EtOAc. The organic phase is then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of 0 to 10% MeOH. 4.8 g of methyl 2-formyl-3-(pyridin-3-yl)propanoate are obtained in the form of a white solid.
Aufarbeitung
- additionis added dropwise, at 0° C. under argon
- extractionextracted with 100 mL of Et2O
- extractionextracted with 2×300 mL of EtOAc
- dry with materialThe organic phase is then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue obtained
- customis purified by chromatography on a column of silica gel
- washeluting with a DCM/MeOH gradient of 0 to 10% MeOH
Quellen und Nachweise
- ORD-Eintrag
- ord-0f1cea3123f047218baadf1b8123047d
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541455B2
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