ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate → Ethyl 7-hydroxychromane-2-carboxylate

HRID 989278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989278
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=O)[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[CH:3]=1>C(O)(=O)C.CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:6][CH2:7][CH:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9]2)=[CH:16][CH:17]=1

Komponenten

5

Edukt 1

HCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Produkt 1

HCID 11085381Ethyl 7-hydroxychromane-2-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of ethyl 7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate (19.0 g, 0.081 mol) in acetic acid is hydrogenated over 10% Pd/C (4.5 g) at 50 psi H2 for 16 hr at ambient temperatures. The catalyst is removed by filtration and the filtrate is concentrated in vacuo to give a residue. The residue is dissolved in EtOAc, washed with saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo to give a solid residue. Crystallization of the solid from CCl4 affords the title compound as an off-white solid, 17.2 g (96% yield), mp 78-80° C., identified by NMR and mass spectral analyses.

Aufarbeitung

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto give a residue
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a solid residue
  8. customCrystallization of the solid from CCl4

Quellen und Nachweise

ORD-Eintrag
ord-f1d2eab842ab4792ba56b5a8378fdff4
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638972B2

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