Dimethylformamide → trans-2-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl) acetonitrile
Reaktionsgleichung
CS(O[CH2:6][C@@H:7]1[CH2:9][C@H:8]1[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)=O.[C-]#N.[K+].[CH3:32][N:33](C=O)C>O>[Si:12]([O:11][CH2:10][C@@H:8]1[CH2:9][C@H:7]1[CH2:6][C:32]#[N:33])([C:25]([CH3:26])([CH3:27])[CH3:28])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of trans-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate (1.23 g, 2.94 mmol), potassium cyanide (0.383 g, 5.88 mmol) and DMF (10 mL) was stirred overnight at 60° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→60% ethyl acetate/hexane) to give trans-2-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)acetonitrile (0.970 g, 2.78 mmol, 94%) as a colorless oil.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10→60% ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-7a7092ac1a1f423aa3bf29153142d695
- Quelldatensatz
- uspto-grants-2016_06
- Patentnummer
- US09365520B2
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