Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol
Reaktionsgleichung
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:14]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15]>CN(C)C=O>[Si:6]([O:15][C:14]1[CH:16]=[C:17]([OH:18])[CH:19]=[CH:20][CH:21]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
Imidazole (4.3 g, 62 mmol) and t-butyldimethylsilylchloride (5.5 g, 36 mmol) were added to a solution of resorcinol (2.8 g, 25 mmol) and dimethylformamide (100 mL) in a 250 mL round bottom flask under a nitrogen atmosphere at room temperature. The solution was heated in a 60° C. oil bath and allowed to stir for 2 hours. The resulting mixture was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 2.7 g (48%) of 3-((t-butyldimethylsilyl)oxy)phenol.
Aufarbeitung
- temperatureThe resulting mixture was cooled to room temperature
- customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
- extractionextracted with ethyl acetate (3×200 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-a8f318088b80435fb2e086e587c84376
- Quelldatensatz
- uspto-grants-2016_07
- Patentnummer
- US09388153B2
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