Cesium carbonate → 6-[(S)-1-(Tetrahydrofuran-2-yl)methoxy]isochroman-1-one

HRID 1887549Notes

Reaction equation

HRID 1887549 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2.[O:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:18]OS(C)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 18649743(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonateHCID 552751836-Hydroxyisochroman-1-one

Product 1

HCID 666799246-[(S)-1-(Tetrahydrofuran-2-yl)methoxy]isochroman-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-hydroxyisochroman-1-one (332 mg), methanesulfonic acid (S)-1-(tetrahydrofuran-2-yl)methyl ester (284 mg), cesium carbonate (1.28 g) and DMF (8 mL) was heated at 70° C. for 7 hours. The cooled reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried and concentrated. The crude product was purified by chromatography on silica gel. The product with the molecular weight of 248.28 (C14H16O4) was obtained in this way; MS (ESI): 249 (M+H+).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between water and ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel
  6. customThe product with the molecular weight of 248.28 (C14H16O4) was obtained in this way

Sources & evidence

ORD record
ord-f91a2390c60e459fa04270b7426cf131
Source dataset
uspto-grants-2013_08
Patent number
US08501771B2

Reaction notes

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