Sodium hydride → (R)-2((1-(Benzyloxy)propan-2-yl)oxy)-3-bromopyridine
Reaktionsgleichung
[CH2:1]([O:8][CH2:9][C@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:15][C:16]1[C:17](Cl)=[N:18][CH:19]=[CH:20][CH:21]=1>CN(C=O)C>[CH2:1]([O:8][CH2:9][C@H:10]([O:12][C:17]1[C:16]([Br:15])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of (R)-1-(benzyloxy)propan-2-ol (2.0 g, 12 mmol) in dry DMF (5 mL) was added NaH (1.5 g, 36 mmol) at 0 Celsius. The reaction mixture was then stirred for 30 min before adding 3-bromo-2-chloropyridine (2.3 g, 12 mmol) and stirring continued for another 4 h. The reaction was quenched by slow addition of water (10 mL) and the resultant mixture extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered, concentrated to dryness, and the crude product purified by FCC to provide the title compound.