Reaktionsgleichung
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=O)[CH:21]=[N:22][CH:23]=1.O>C1COCC1>[CH3:16][O:17][C:18]1[CH:19]=[C:20](/[CH:24]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:21]=[N:22][CH:23]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a suspension of 3.12 g (78.1 mmol) of sodium hydride (60% in oil) in 30 mL of anhydrous THF is added, over 45 minutes, under argon and at 0° C., 16.4 g (78.1 mmol) of methyl (diethoxyphosphoryl)acetate in 10 mL of THF. Stirring is maintained for 30 minutes at 0° C. and 5.1 g (37.2 mmol) of 5-methoxypyridine-3-carbaldehyde in 20 mL of anhydrous THF are then added dropwise at 0° C. After cooling to room temperature, the reaction mixture is treated with 150 mL of water and then extracted with EtOAc (3×100 mL). The organic phases are combined, washed successively with water (2×20 mL), dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAC gradient of 0 to 40% EtOAc. 1 g of methyl (2E)-3-(5-methoxypyridin-3-yl)prop-2-enoate is obtained in the form of a white powder.
Aufarbeitung
- additionis added, over 45 minutes, under argon and at 0° C.
- temperatureAfter cooling to room temperature
- extractionextracted with EtOAc (3×100 mL)
- washwashed successively with water (2×20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue obtained
- customis purified by chromatography on a column of silica gel
- washeluting with a cyclohexane/EtOAC gradient of 0 to 40% EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-3c00c64361cc4b72abed7773c1bb66fa
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541455B2
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