Diisobutylaluminum hydride → HCID 22226108, Verbindung
Reaktionsgleichung
C(O[C:4](=[O:27])/[C:5](/[F:26])=[C:6](\[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)/[CH3:7])C.[CH3:28]C(C[AlH]CC(C)C)C>C1COCC1>[F:26]/[C:5](=[C:6](/[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)\[CH2:7][CH3:28])/[CH2:4][OH:27]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of(E)-2-fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester (Intermediate 6, 2.2 g, 5.85 mmol) in THF (50 mL) at −78° C. was added DIBAL-H (23.4 mL, 1.0 M in CH2Cl2, 23.4 mmol) over 10 min. After stirring at −78° C. for 3 h, the reaction was quenched with aqueous NH4Cl followed by 1M HCl and was extracted with Et2O (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane) to give the title compound (1.02 g, 45% over 2 steps).
Aufarbeitung
- customthe reaction was quenched with aqueous NH4Cl
- extractionwas extracted with Et2O (×3)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-1b4f710c95f04873b3cbff6dbf6ca583
- Quelldatensatz
- uspto-grants-2004_07
- Patentnummer
- US06759547B1
Notizen zur Reaktion
Wird geladen…