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

HRID 69499

Reaktionsgleichung

Reaktionsgleichung von HRID 69499
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b450f26fa40345c3a2ee6e4962b671cd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822495B2

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