Reaktionsgleichung
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.II.[O:19]1[CH:21]([CH3:22])[CH2:20]1.[NH4+].[Cl-]>C1COCC1>[Si:8]([O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([CH2:20][CH:21]([OH:19])[CH3:22])=[CH:3][CH:4]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of (4-bromobenzyloxy)(tert-butyl)dimethylsilane (3.080 g) in THF (20 mL) were added Mg (0.288 g) and I2 (cat) at room temperature under an Ar atmosphere. The mixture was heated at 50° C. for 1 hour, and then cooled to room temperature. To the mixture was added 1,2-epoxypropane (0.77 mL) at room temperature under an Ar atmosphere, and the mixture was stirred at room temperature for 14.5 hours, and then heated at 50° C. for 1 hour, and then cooled to room temperature. To the mixture was added saturated aqueous NH4Cl, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford 1-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-ol (1.485 g) as a colorless oil.
Aufarbeitung
- temperaturecooled to room temperature
- temperatureheated at 50° C. for 1 hour
- temperaturecooled to room temperature
- extractionthe mixture was extracted with AcOEt
- washThe organic layer was washed with saturated aqueous NaCl
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-3bbe2a901c9b43e794b12ea9324b81fc
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08722663B2
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