Water → 6-[(R)-1-(Tetrahydrofuran-2-yl)methoxy]isochromen-1-one

HRID 1887542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887542
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7]S(C)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[O:24][CH:23]=[CH:22]2.O>CN(C=O)C>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[O:24][CH:23]=[CH:22]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 266119(Tetrahydrofuran-2-yl)methyl methanesulfonateHCID 668796996-Hydroxyisochromen-1-one

Produkt 1

HCID 668789366-[(R)-1-(Tetrahydrofuran-2-yl)methoxy]isochromen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methanesulfonic acid tetrahydrofuran-2-ylmethyl ester (2.7 g) and cesium carbonate (12 g) were added to a solution of 6-hydroxyisochromen-1-one (2 g) in DMF (50 mL) and the mixture was stirred at 80° C. for 7 h. After addition of water, the mixture was extracted with dichloromethane, dried over magnesium sulfate and concentrated. The product with the molecular weight of 246.27 (C14H14O4) was obtained in this way; MS (ESI): 247 (M+H+). 6-[(R)-1-(Tetrahydrofuran-2-yl)methoxy]isochromen-1-one was synthesized analogously.

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 246.27 (C14H14O4) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-79b0d73904a642d8a184a9388cbecde8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501771B2

Notizen zur Reaktion

Wird geladen…