Reaktionsgleichung
FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O.[CH:18]([Si:21]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[O:22][CH2:23][C@@H:24]([OH:26])[CH3:25])([CH3:20])[CH3:19].[O:33]1[CH2:35][C@@H:34]1[C:36]([O:38][CH3:39])=[O:37]>C(OCC)(=O)C>[OH:33][C@H:34]([CH2:35][O:26][C@@H:24]([CH3:25])[CH2:23][O:22][Si:21]([CH:18]([CH3:20])[CH3:19])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:32])[CH3:31])[C:36]([O:38][CH3:39])=[O:37]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Magnesium trifluoromethanesulfonate (1.263 g, 3.92 mmol) was added to a mixture of (S)-1-(triisopropylsilyloxy)propan-2-ol (4.55 g, 19.59 mmol) and (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) in ethyl acetate (40 mL). The resulting suspension was heated to 80° C. for 72 hours. Further (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) was added and the mixture stirred at 80° C. for 48 hrs. Further (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) was added and the mixture stirred for 24 hrs. The mixture was allowed to cool, filtered through a bed of silica (˜10 g), washed through with EtOAc and evaporated. The crude product was purified by flash silica chromatography, elution gradient 10 to 50% EtOAc in isohexane, to afford the product (2.7 g, 41%).
Aufarbeitung
- stirringthe mixture stirred for 24 hrs
- temperatureto cool
- filtrationfiltered through a bed of silica (˜10 g)
- washwashed through with EtOAc
- customevaporated
- customThe crude product was purified by flash silica chromatography, elution gradient 10 to 50% EtOAc in isohexane
Quellen und Nachweise
- ORD-Eintrag
- ord-786616f159c04a1491d48599f08480bf
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08071608B2
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