Reaktionsgleichung
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:2].O1CCCC1.C(O[K])(C)(C)C.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][CH2:33]Br)[CH:27]=1>O.CN(C)C=O>[Br:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][CH:3]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[C:1]#[N:2])[CH:29]=[CH:30][CH:31]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a mixed solution of methyl 4-(cyanomethyl)benzoate (3.50 g, 20.0 mmol), tetrahydrofuran (25 mL) and N,N-dimethylformamide (10 ml) was added tert-butoxy potassium (2.69 g, 24.0 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added 1-bromo-3-(2-bromoethyl)benzene (3.37 mL, 22.0 mmol) at the same temperature, and the mixture was stirred under ice-cooling for 4 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (3.94 g, 55%) as a colorless oil.
Aufarbeitung
- stirringthe mixture was stirred under ice-
- temperaturecooling for 4 hr
- extractionextracted with ethyl acetate
- washwashed successively with water and saturated brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-42dd959c09e7445aa431ff3d0d1e2b41
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08461348B2
Verknüpfte Notizen
Wird geladen…