2-Hydroxyxanthone → Pentanoic acid, 5-[(9-oxo-9H-xanthen-2-yl)oxy]-, ethyl ester

HRID 1197192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197192
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C>[O:16]=[C:5]1[C:4]2[CH:3]=[C:2]([O:1][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Komponenten

5

Edukt 3

HCID 747082-HydroxyxanthoneHCID 84580Ethyl 5-bromovalerateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 2818242Pentanoic acid, 5-[(9-oxo-9H-xanthen-2-yl)oxy]-, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-hydroxyxanthone (7.7 g, 36 mmol) prepared as described in Example 1, was dissolved in DMF (50 mL), and potassium tert-butoxide (4.6 g, 41 mmol) was added in one portion. The mixture was stirred under N2 at 25° C. for 1.5 hours, and then ethyl 5-bromovalerate (8.74 g, 42 mmol) in DMF (20 mL) was added dropwise over 20 minutes. The reaction mixture was heated at 115° C. for 11 hours, then cooled, filtered, and washed with EtOAc (2×10 mL). The filtrate was concentrated to provide a light-brown oily residue, which slowly solidified at room temperature. Light-beige crystals were collected and washed with n-hexane (3×10 mL). TLC pure, Rf =0.79 benzene-EtOH 10:9. Yield: 9.70 g (79%). A small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis. White needles, 1H-NMR (CDCl3 δ: 8.34 (dd, J=1.6 and 8.0 Hz, 1H), 7.66-7.76 (m, 2H, 7.3-7.5 (m, 4H), 4.14 (q, J=7.1 Hz, 2H), 2.40 [t,J=6.9 Hz, 2H, CH2 (C=0)] 1.85 (m, 4H), 1.26 (t,J=7.1 Hz, 3H-CH3).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 115° C. for 11 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washwashed with EtOAc (2×10 mL)
  5. concentrationThe filtrate was concentrated
  6. customto provide a light-brown oily residue, which
  7. customslowly solidified at room temperature
  8. customLight-beige crystals were collected
  9. washwashed with n-hexane (3×10 mL)
  10. customA small amount of the product was recrystallized from n-hexane-EtOH (10:1) for elemental analysis

Quellen und Nachweise

ORD-Eintrag
ord-ce0915c9f9ab42188146a79c6d73c142
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05117009

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