2-Ethylbutyraldehyde → HCID 68593352, Verbindung
Reaktionsgleichung
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH2:18]([CH:20]([CH2:23][CH3:24])[CH:21]=[O:22])[CH3:19].[NH4+].[Cl-]>CCOCC>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:21]([OH:22])[CH:20]([CH2:23][CH3:24])[CH2:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a chilled reaction vessel at −45° C. containing 1-benzyl-1H-imidazole (3.0 g, 19.0 mmol) in Et2O (100 mL) was added a solution of n-butyllithium (2.5M in hexanes, 10.8 mL, 26.9 mmol) dropwise. After 30 min, the reaction vessel was cooled to −78° C. and 2-ethylbutyraldehyde (2.8 mL, 22.8 mmol) was added dropwise. The reaction mixture was warmed to 0° C. and stirred for 15 min, then poured into sat. aqueous NH4Cl and extracted with Et2O. The organic layer was washed with H2O, dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2, then 7:3) to yield a clear oil in 69% yield.
Aufarbeitung
- customTo a chilled reaction vessel at −45° C.
- temperatureThe reaction mixture was warmed to 0° C.
- extractionextracted with Et2O
- washThe organic layer was washed with H2O
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2
- custom7:3) to yield a clear oil in 69% yield
Quellen und Nachweise
- ORD-Eintrag
- ord-22ef515c1a0e407fae3abea73fd0f058
- Quelldatensatz
- uspto-grants-2008_07
- Patentnummer
- US07399778B2
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