Acetaldehyde → HCID 12874036, Verbindung
Reaktionsgleichung
C([N-]C(C)C)(C)C.[Li+].[O:9]=[C:10]1[N:17]2[C:12]([CH3:20])([CH2:13][CH2:14][O:15][C:16]2([CH3:19])[CH3:18])[CH2:11]1.[CH:21](=[O:23])[CH3:22].[Cl-].[Na+]>O1CCCC1.O>[O:9]=[C:10]1[N:17]2[C:12]([CH3:20])([CH2:13][CH2:14][O:15][C:16]2([CH3:19])[CH3:18])[CH:11]1[CH:21]([OH:23])[CH3:22]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 1.1 equivalents of freshly prepared lithium diisopropylamide in anhydrous tetrahydrofuran under a nitrogen atmosphere at -78° is added a solution of 8-oxo-2,2,6-trimethyl- 3-oxa-1-azabicyclo[4.2.0]octane in anhydrous tetrahydrofuran which has been cooled to -78° C. After two minutes, the resulting lithium enolate is treated with excess acetaldehyde. The solution is stirred for 30 minutes at -78° and then poured into water. The aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The combined ethyl acetate solutions are dried over magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure to give the crude product. Purification by chromatography on silica gel using ethylacetate/benzene gives 8-oxo-2,2,6-trimethyl-7-(1-hydroxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane.
Aufarbeitung
- extractionextracted with ethyl acetate
- dry with materialThe combined ethyl acetate solutions are dried over magnesium sulfate
- filtrationfiltered
- customThe filtrate is evaporated under reduced pressure
- customto give the crude product
- customPurification by chromatography on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-a510198c04074f4ca00c9773351d2b2a
- Quelldatensatz
- uspto-grants-1981_04
- Patentnummer
- US04264621
Notizen zur Reaktion
Wird geladen…