Water → 6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]isochromen-1-one

HRID 1913830Notes

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][CH:6]=[CH: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+].O>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][CH:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-hydroxyisochromen-1-one (2 g) in DMF (50 ml) were added methanesulfonic acid (S)-1-(tetrahydrofuran-2-yl)methyl ester (2.7 g) and cesium carbonate (12 g), and the mixture was stirred at 80° C. for 7 hours. After water had been added, the mixture was extracted with dichloromethane. The organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 246.27 (C14H14O4); MS (ESI): 247 (M+H+).

Workup

extractionthe mixture was extracted with dichloromethane
dry with materialThe organic phases were dried over magnesium sulfate
concentrationconcentrated
customThe product was thus obtained with the molecular weight of 246.27 (C14H14O4)

Sources & evidence

ORD record: ord-845ddf2eb1354a338834718f55a67c95
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609731B2

Reaction notes

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