Ethyl trimethylsilylacetate → Ethyl 3-(1-methyl-1H-imidazol-5-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate
Reaktionsgleichung
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(C)C.[CH3:21][N:22]1[C:26]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[CH:31][CH:30]=2)=O)=[CH:25][N:24]=[CH:23]1>C1COCC1>[CH3:21][N:22]1[C:26]([C:27]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)=[CH:33][CH:34]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:25][N:24]=[CH:23]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -45 °C
Versuchsvorschrift
To a solution of lithium bis(trimethylsilyl)amide (6.8 mmol, 1 M in THF) was added ethyl trimethylsilylacetate (6.5 mmol) dropwise at −78° C. After 20 minutes at −78° C., a solution of 74.2 (5.9 mmol) in THF (20 mL) was added dropwise. The reaction was maintained at −78° C. for 3 hours and at −45° C. for 2 hours. The reaction was quenched with saturated NH4Cl (aq) at 0° C. and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford crude 74.3 (2.49 g). MS ESI (pos.) m/e 357.2 (M+H).
Aufarbeitung
- customThe reaction was quenched with saturated NH4Cl (aq) at 0° C.
- temperaturewarmed to room temperature
- extractionThe mixture was extracted with EtOAc (500 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-d76b189b63724601a6cd10248700550d
- Quelldatensatz
- uspto-grants-2009_09
- Patentnummer
- US07582803B2
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