7,8-Dihydroxyflavone → HCID 59052279, Verbindung

HRID 734188

Reaktionsgleichung

Reaktionsgleichung von HRID 734188
[OH:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:19])[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.Cl[C:21]([CH3:25])([CH3:24])[C:22]#[CH:23].N12CCCN=[C:32]1[CH2:31][CH2:30][CH2:29]CC2.[C:37](#N)C>>[CH3:24][C:21]([CH3:25])([O:1][C:2]1[C:11]([O:12][C:31]([CH3:32])([CH3:37])[C:30]#[CH:29])=[C:10]2[C:5]([C:6](=[O:19])[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1)[C:22]#[CH:23]

Komponenten

5

Edukt 4

HCID 18807,8-DihydroxyflavoneHCID 6342AcetonitrileHCID 706791-Butyne, 3-chloro-3-methyl-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 59052279HCID 59052279, VerbindungAusbeute 69 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 7,8-dihydroxy-2-phenyl-chromen-4-one (510 mg, 2 mmol) and CuCl2 (16 mg, 0.12 mmol) in acetonitrile (3 mL) was added 3-chloro-3-methyl-1-butyne (0.5 mL, 4.56 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.78 mL, 5.2 mmol) slowly at 0° C. The dark mixture was stirred at 0° C. for 5 h and then at room temperature overnight. The solvent was evaporated and the residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-50%) to give the title compound as a white solid (540 mg, 69%): 1H NMR (CDCl3, 300 MHz) δ 8.02 (m, 2H), 7.96 (d, J=9.0 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.53 (m, 3H), 6.78 (s, 1H), 2.66 (s, 1H), 2.26 (s, 1H), 1.81 (s, 6H), 1.76 (s, 6H).

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography (SiO2, EtOAc:hexanes/10-50%)

Quellen und Nachweise

ORD-Eintrag
ord-9bcbb5461b234b19b6e606b26e50ecfb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592143B2

Verknüpfte Notizen

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