Sodium hydride → 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone
Reaktionsgleichung
[H-].[Na+].Cl.[NH:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1.[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl>C1COCC1>[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a suspension of sodium hydride (3.07 g, 76.75 mmol) in 100 mL of anhydrous THF cooled to 0° C. under N2 (g) inlet was added 1-(1H-pyrazole-5-yl)ethan-1-one hydrochloride (3.09 g, 21.08 mmol). After warming to rt over 1 h, a solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.5 mL, 25.43 mmol) in 100 mL of anhydrous THF was added to the reaction flask via cannulation. The reaction was quenched with water and extracted with EtOAc after 2 h. The organic phase was collected, dried with sodium sulfate, filtered and concentrated under reduced pressure followed by purification by flash chromatography (silica, 50:50 EtOAc/hexane) to give 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone. LCMS; 241.1 m/z (M+H)+.
Aufarbeitung
- temperatureAfter warming to rt over 1 h
- customThe reaction was quenched with water
- extractionextracted with EtOAc after 2 h
- customThe organic phase was collected
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customfollowed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-ea914fe853d74367874e191c8643a112
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08445503B2
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