Ammonium Chloride → HCID 23144601, Verbindung
Reaktionsgleichung
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24].C([Mg]Cl)(C)C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]([N:22]([O:23][CH3:24])[CH3:21])=[O:17])[CH2:13][CH2:14]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Ethyl 4-(tert-butyldimethylsilyloxy)cyclohexane-carboxylate (5.73 g, 20.0 mmol) obtained in Step 1 and N,O-dimethylhydroxylamine hydrochloride (2.93 g, 30.0 mmol) were suspended in THF (40 mL), and a 2.0 mol/L solution of isopropylmagnesium chloride in THF (30.0 mL, 60.0 mmol) was added dropwise thereto in a atmosphere of argon at −20° C., followed by stirring at 0° C. for 1 hour. A saturated aqueous solution of ammonium chloride and ethyl acetate were added to the reaction mixture for extraction. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4) to afford 4-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclo-hexanecarboxamide (6.03 g, 100%).
Aufarbeitung
- customat −20° C.
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away under reduced pressure
- customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4)
Quellen und Nachweise
- ORD-Eintrag
- ord-39792b5ad12b40f8af59beb070cd0ee3
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08889718B2
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