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

HRID 1887542Notes

Reaction equation

HRID 1887542 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79b0d73904a642d8a184a9388cbecde8
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

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