Metaperiodic acid → 3-Hydroxy-6-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-isochroman-1-one

HRID 69499

Reaction equation

I(O)(=O)(=O)=[O:2].[OH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH2:17][C@H:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[CH:13]=2)[C:8]1=[O:23]>O.O.C1COCC1>[OH:2][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH2:17][C@H:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[CH:13]=2)[C:8](=[O:23])[O:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of periodic acid in water (0.5 M; 5.2 mL) was added at 0° C. to a solution of 2-hydroxy-5-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-indan-1-one (581 mg) in water/THF 1:1 (12 mL) and the solution was stirred at 0° C. for 1 h. After adding water it was extracted with ether, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 264.28 (C14H16O5); MS (ESI): 265 (M+H+).

Workup

extractionwas extracted with ether
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by preparative HPLC
customIn this way the product was obtained with molecular weight 264.28 (C14H16O5)

Sources & evidence

ORD record: ord-b450f26fa40345c3a2ee6e4962b671cd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Linked notes

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