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

HRID 69499
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 689880982-hydroxy-5-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-indan-1-one

Product 1

HCID 689918573-Hydroxy-6-[(R)-1-(tetrahydrofuran-2-yl)methoxy]-isochroman-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

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

  1. extractionwas extracted with ether
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes