Potassium Iodide → 6-(cyclopentyloxy)-7-hydroxy-2H-1-benzopyran-2-one

HRID 22361

Reaktionsgleichung

Reaktionsgleichung von HRID 22361
[OH:1][C:2]1[C:3]([O:13]CC2C=CC=CC=2)=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=2[CH:12]=1.[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH:21]1([O:1][C:2]2[C:3]([OH:13])=[CH:4][C:5]3[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=3[CH:12]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12045357-(benzyloxy)-6-hydroxy-2H-chromen-2-one

Produkt 1

HCID 199277426-(cyclopentyloxy)-7-hydroxy-2H-1-benzopyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

50.0 g (186 mmol) of 6-hydroxy-7-phenylmethoxy-2H-1-benzopyran-2-one, 41.7 g (280 mmol) of cyclopentylbromide, 51.4 g (372 mmol) of potassium carbonate and 5.0 g of potassium iodide are agitated in 500 ml DMF for 18 h at 80° C. This is followed by filtration, evaporation, dissolution in chloroform, washing with water, drying over sodium sulfate and renewed evaporation: yield: 60.0 g (96%) of 6-(cyclopentyloxy)-7-(phenylmethoxy)-2H-1-benzopyran-2-one, fusion point 140°-141° C. (from isopropanol). Of this 15.0 g (45 mmol) in 200 ml ethanol are hydrogenated in the presence of 2.0 g Pd on active carbon (5%) for 3 h at 25° C. and 7 bar hydrogen pressure. After filtration the solvent is removed: yield 9.0 g (82%), fusion point 154°-155° C. (from isopropanol and TBME).

Aufarbeitung

  1. filtrationThis is followed by filtration, evaporation, dissolution in chloroform
  2. washwashing with water
  3. dry with materialdrying over sodium sulfate
  4. customevaporation
  5. customyield: 60.0 g (96%) of 6-(cyclopentyloxy)-7-(phenylmethoxy)-2H-1-benzopyran-2-one, fusion point 140°-141° C. (from isopropanol)
  6. filtrationAfter filtration the solvent
  7. customis removed
  8. customyield 9.0 g (82%), fusion point 154°-155° C. (from isopropanol and TBME)

Quellen und Nachweise

ORD-Eintrag
ord-fdec0f046a2d4bc29dd9bda843e2c9dd
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428038

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