Sodium borohydride → (5-Chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol
Reaktionsgleichung
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:22]=[O:23])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])=[N:7]2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:22][OH:23])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:20])([F:21])[F:19])=[N:7]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 5-chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (2.1673 g, 6.456 mmol) in 32 mL of THF at 0° C. was added sodium borohydride (0.3664 g, 9.684 mmol) and the mixture was stirred at 0° C. After 1 hr at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (50 mL×3), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (5-chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.73 (1 H, m), 7.96-8.02 (1 H, m), 7.90-7.95 (1 H, m), 7.83-7.87 (1 H, m), 7.68-7.83 (3 H, m), 7.50-7.58 (1 H, m), 5.63 (1 H, t, J=5.3 Hz), 4.36 (2 H, br. s.); LC-MS (ESI) m/z 338.0 [M+H]+. The product was carried on crude without purification for the next step.
Aufarbeitung
- customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
- washthe organic layer was washed with brine (50 mL×3)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-20b9747a3e4b47ae81d1a6a1d3a25aa9
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07919498B2
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