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

HRID 1913839Notes

Reaction equation

HRID 1913839 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 to 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 was thus obtained with the molecular weight of 248.28 (C14H16O4); 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 was thus obtained with the molecular weight of 248.28 (C14H16O4)

Sources & evidence

ORD record
ord-479277afa50642e5ab09e55d4fed40ca
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

Loading…