6-Methylchromone-2-carboxylic Acid → 6-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

HRID 1662143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662143
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6][C:5]2=O>[Pd].C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6][CH2:5]2

Komponenten

4

Edukt 1

HCID 6887046-Methylchromone-2-carboxylic Acid

Produkt 1

HCID 203830736-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

6-Methyl-4-oxo-4H-chromene-2-carboxylic acid (Aldrich, 3.5 g, 17.1 mmol) was added to a mixture of acetic acid (50 mL) and 10% palladium on carbon (0.35 g) in a Parr shaker. The glass reactor was sealed and flushed with nitrogen, and pressurized with hydrogen (60 psi). The mixture was shaken at 70° C. for 2.5 hours, and filtered and solids were rinsed with methanol. The filtrate was concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.09-2.23 (m, 1H), 2.25 (s, 3H), 2.28-2.40 (m, 1H), 2.72-2.86 (m, 2H), 4.71 (dd, J=8.48, 3.39 Hz, 1H), 6.83 (t, J=8.65 Hz, 2H), 6.90-6.96 (m, 1H). MS (ESI) m/z 210.1 (M+NH4)+.

Aufarbeitung

  1. customThe glass reactor was sealed
  2. customflushed with nitrogen
  3. filtrationfiltered
  4. washsolids were rinsed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1c554a490873476d9c21e5a4e6c6197b
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030504B2

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