Dimethylformamide → 2,6-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde
Reaktionsgleichung
Br[C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[CH3:17].[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[CH3:17][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:14]=[C:15]([CH3:16])[C:2]=1[CH:26]=[O:27]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 1-[2-(4-bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine (176 mg) in THF (5 mL) was added n-BuLi (1.36 mL, 1.0 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 30 min, allowed to warm up to −40° C. for 5 min, and then cooled down to at −78° C. After 20 min. DMF (0.24 mL) was added. The mixture was stirred at −78° C. for 30 min and then allowed to warm up to room temperature for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde: MS (m/z) 248 (M+1).
Aufarbeitung
- temperatureto warm up to −40° C. for 5 min
- temperaturecooled down to at −78° C
- waitAfter 20 min
- stirringThe mixture was stirred at −78° C. for 30 min
- temperatureto warm up to room temperature for 1 h
- customThe reaction was quenched with saturated NH4Cl aqueous solution
- extractionextracted with EtOAc
- washThe organic extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-31873e92ec6e47d283e84029681b3008
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08222248B2
Notizen zur Reaktion
Wird geladen…