Potassium Carbonate → (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane
Reaktionsgleichung
[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[F-].[Cs+].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=C(S(O[CH2:37][C@H:38]2[O:40][CH2:39]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.O>[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][C@H:38]2[O:40][CH2:39]2)=[CH:11][CH:10]=1)([CH3:3])[CH3:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
p-(2-Isopropoxyethoxy)methylphenol (5 g) was dissolved in DMF (30 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Cesium fluoride (0.72 g) and potassium carbonate (4.27 g) were added thereto, and the mixture was stirred for 1 hour. Then (S)-glycidyl m-nitrobenzenesulfonate (6.16 g, 99.7% e.e.) was added thereto and the mixture was stirred for 24 hours at the same temperature. After the reaction, water was added to the filtrate, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 1:1) to give 6.08 g of (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane (yield 96%, optical purity 99.6% e.e.) as a colorless oil.
Aufarbeitung
- stirringthe mixture was stirred for 24 hours at the same temperature
- additionwas added to the filtrate
- extractionthe solution was extracted with ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate, condensed
Quellen und Nachweise
- ORD-Eintrag
- ord-7318814ed964412b8fcab9e74ef7d2b0
- Quelldatensatz
- uspto-grants-2000_07
- Patentnummer
- US06087512
Notizen zur Reaktion
Wird geladen…