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1-Benzofuran-5-carbaldehyde → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenone

HRID 355345
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 355345
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=1[C:32](=[O:34])[CH3:33])(=O)C.[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([CH:44]=O)[CH:42]=[CH:43][C:36]1=2>C(O)C.C(O)(=O)C.[C].[Pd]>[C@@H:6]1([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=2[C:32](=[O:34])[CH2:33][CH2:44][C:41]2[CH:42]=[CH:43][C:36]3[O:35][CH2:39][CH2:38][C:37]=3[CH:40]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 27738751-Benzofuran-5-carbaldehydeHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone

Produkt 1

HCID 117976222'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenoneAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysator
HCID 176
Acetic Acid
Lösungsmittel
HCID 702EthanolLösungsmittel

Versuchsvorschrift

2'-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (1268 mg) and benzo[b]furan-5-carbaldehyde (911 mg) are treated in the same manner as in Example 1 to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone. This product is dissolved in a mixture of ethanol (20 ml) and acetic acid (2 ml), and the mixture is subjected to catalytic hydrogenation by using 10% palladium-carbon (0.5 g) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. To the residue are added ethyl acetate and water, and the mixture is stirred. The organic layer is collected, washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and evaporated to remove the solvent. The residue is pulverized with chloroform-diisopropyl ether, and the obtained powder is collected by filtration and dried to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(2,3-dihydro-5-benzo[b]furanyl)propiophenone (920 mg).

Aufarbeitung

  1. customto give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionTo the residue are added ethyl acetate and water
  5. customThe organic layer is collected
  6. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. filtrationthe obtained powder is collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-628431c8253e4dfcbc37107b1f46b615
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05830873

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