Tetrabutylammonium Fluoride → Tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate
Reaktionsgleichung
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])=[CH:9][CH:8]=1)#[CH:5]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (10.1 g, 29.4 mmol) in anhydrous tetrahydrofuran (150 ml) was added at 0° C. tetra-n-butylammonium fluoride (1M tetrahydrofuran solution, 29.4 ml, 29.4 mmol). After stirring at 0° C. for 45 mins, the mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate, and the extract was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate (7.7 g, yield 96%) as a yellow solid.
Aufarbeitung
- concentrationthe mixture was concentrated under reduced pressure
- additionWater was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- concentrationthe extract was concentrated under reduced pressure
- customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-6994e59836124459a8ef6dd20e9ad3e5
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US08999989B2
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