Ammonium Chloride → 5-[2-(1,3-Difluoro-2-methylpropan-2-yl)oxiran-2-yl]-1,3-thiazole
Reaktionsgleichung
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.C([Li])CCC.Br[CH2:16][C:17](=[O:24])[C:18]([CH2:22][F:23])([CH3:21])[CH2:19][F:20].[Cl-].[NH4+]>C(OCC)C>[F:20][CH2:19][C:18]([C:17]1([C:5]2[S:4][CH:3]=[N:7][CH:6]=2)[CH2:16][O:24]1)([CH3:21])[CH2:22][F:23]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To 2.00 g (12.7 mmol) of 2-trimethylsilyl-1,3-thiazole dissolved in 20 ml of diethyl ether were added, at −78° C. under an argon atmosphere, 5.1 ml (2.5 M, 12.7 mmol) of n-butyllithium, and the reaction mixture was stirred at −78° C. for 20 min. Then 2.73 g (12.7 mmol) of 1-bromo-4-fluoro-3-(fluoromethyl)-3-methylbutan-2-one were added and the reaction mixture was gradually warmed to room temperature. After addition of saturated aqueous ammonium chloride solution, the phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The crude product was then purified by column chromatography (5:1 cyclohexane/ethyl acetate). This gave 2.39 g (86%) of the desired product.
Aufarbeitung
- additionwere added, at −78° C. under an argon atmosphere
- customthe phases were separated
- extractionthe aqueous phase was extracted with diethyl ether
- dry with materialThe combined organic phases were dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was then purified by column chromatography (5:1 cyclohexane/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-117fbc51cf844377a02838d13a8c49cb
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08440836B2
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