Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate
Reaktionsgleichung
[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 23 °C
Versuchsvorschrift
To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T37.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield T37.3 as a colorless solid (0.307 g, 77% yield).
Aufarbeitung
- concentrationThe reaction was then concentrated in vacuo
- additionThe reaction was diluted with 1N HCl
- extractionextracted three times with EtOAc
- dry with materialAfter drying over anhydrous magnesium sulfate
- filtrationfiltering
- customthe organic solvent was removed under reduced pressure
- customthe product was then purified on silica gel (0-40% EtOAc in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-740c0c42973f45e4963bc04053215a52
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08450522B2
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