Diisobutylaluminum hydride → 2-(6-Chloropyridin-2-yl)ethanol
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9](OCC)=[O:10])[N:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][OH:10])[N:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Ester 30-1 (1.34 g, 6.7 mmol) was dissolved in 10 mL CH2Cl2 at -78°, DIBAL (1M in CH2Cl2, 17 mL, 17 mmol) was added, the mixture was warmed to RT for 15 min before quenching in a mixture of 25 mL saturated aqueous Na-K tartrate and 100 mL EtOAc. This mixture was shaken vigorously. The phases were allowed to separate, and the organic layer was washed with brine, dried (MgSO4), concentrated and chromatographed (silica, 40% EtOAc/hexane), providing 30-2 as a yellow oil.
Aufarbeitung
- custombefore quenching in a mixture of 25 mL saturated aqueous Na-K tartrate and 100 mL EtOAc
- customto separate
- washthe organic layer was washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customchromatographed (silica, 40% EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-4e935d9421444d4aae4963d5d0c851b2
- Quelldatensatz
- uspto-grants-1999_07
- Patentnummer
- US05929120
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