2-(4-Oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione → 2-(4-Oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione

HRID 965938

Reaktionsgleichung

Reaktionsgleichung von HRID 965938
[O:1]=[C:2]1[CH:7]=[CH:6][O:5][CH:4]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH2:3]1.[H][H]>C(OCC)(=O)C.[Pd]>[O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH:4]([CH2:8][N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])[CH2:3]1

Komponenten

5

Edukt 2

HCID 219366682-(4-Oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 219367872-(4-Oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dioneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(4-Oxo-3,4dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione (13 g, 0.051 mol) was dissolved in ethyl acetate (250 ml) and placed in a Parr bottle. 10% Pd/C (1.5 g) was carefully added and the mixture was shaken under a pressure of 30 psi of hydrogen for 6.5 h (Parr apparatus). Filtration followed by evaporation of the ethyl acetate in vacuo afforded a crude 11.5 g of 2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione pure enough for the next step. Analytical pure compound could be obtained by purification of a small sample (250 mg) by column chromatography on silica gel, utilising a mixture of hexane/ethyl acetate as a gradient (from 100/0 to 50/50). Pure fractions were collected and the solvent evaporated in vacuo affording 142 mg (55%) of 2-(4-oxo-tetrahydro-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.

Aufarbeitung

  1. filtrationFiltration
  2. customfollowed by evaporation of the ethyl acetate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a4bccce14247485f901151a1e04f0a16
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951878B2

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