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Ethyl 4-oxo-4H-1-benzopyran-2-carboxylate → Ethyl Chroman-2-carboxylate

HRID 1603869
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1603869
O=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3]1>CO.C(Cl)(Cl)Cl.C(O)(=O)C.[Pd]>[O:5]1[C:6]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 1

HCID 26861Ethyl 4-oxo-4H-1-benzopyran-2-carboxylate

Produkt 1

HCID 12909094Ethyl Chroman-2-carboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel
HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

A solution of ethyl 4-oxo-4H-1-benzopyran-2-carboxylate (2.0 g, 9.17 mmol) in methanol (60 ml), chloroform (25 ml) and glacial acetic acid (20 ml) was added with 10% palladium-on-charcoal and the mixture was left under stirring at room pressure and temperature for 24 h. under hydrogen atmosphere. After that, the catalyst was filtered off and the filtrate was evaporated to dryness. The residue was redissolved in ethyl ether and washed successively with a 5% sodium bicarbonate solution and a sodium chloride saturated solution. The mixture was dried and the solvent was evaporated off under reduced pressure, to obtain 1.575 g of the title product (84% yield).

Aufarbeitung

  1. waitthe mixture was left
  2. filtrationAfter that, the catalyst was filtered off
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was redissolved in ethyl ether
  5. washwashed successively with a 5% sodium bicarbonate solution
  6. customThe mixture was dried
  7. customthe solvent was evaporated off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0493502a233544249da36db96ee3a3b0
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05990142

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