Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C-]#N.[Li+].[CH3:18][N:19](C=O)C>>[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13][C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]Komponenten
4
Versuchsvorschrift
A solution of 1-(4-bromobutyl)cyclopentane carboxlic acid methyl ester was treated with a solution of 0.5 molar lithium cyanide in DMF (5 mmol, 10 mL) and stirred overnight at room temperature followed by heating at 75° C. for two hrs. The reaction mixture was evaporated to dryness, the residue was dissolved in ethyl acetate (30 mL) and washed with sat'd sodium bicarbonate (2×10 mL), and brine (5 mL) and dried over magnesium sulfate to give a yellow oil (860 mg). Silica gel chromtography eluting with 1:3 ethyl acetate:hexane yielded a pale oil (83%, 693 mg). LR MS (C12H19NO2): Obs mass, 227 (M+NH4), 248 (M+K).
Aufarbeitung
- temperatureby heating at 75° C. for two hrs
- customThe reaction mixture was evaporated to dryness
- dissolutionthe residue was dissolved in ethyl acetate (30 mL)
- washwashed with sat'd sodium bicarbonate (2×10 mL), and brine (5 mL)
- dry with materialdried over magnesium sulfate
Quellen und Nachweise
- ORD-Eintrag
- ord-454bd1f896f247ae87245201914af0bc
- Quelldatensatz
- uspto-grants-2004_10
- Patentnummer
- US06806365B2
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