Diethyl Ether → Ethyl [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 346709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346709
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=O)[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2].CCOCC>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][CH:19]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2]

Komponenten

5

Edukt 2

HCID 3283Diethyl EtherHCID 20761976Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

Produkt 1

HCID 20761975Ethyl [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetateAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (33 g, 73 mmol) and zinc (90 g, 1.38 mol) were refluxed in acetic acid for 66 h. An additional quantity of zinc (25 g, 0.38 mol) was added and reflux continued for 18 h. The mixture was filtered hot and the filtrate was evaporated to a yellow solid. The solid was purified by 800 g Biotage column eluting with 20% ethyl acetate/hexane to give a white solid, which was triturated in ether to give a white solid. A further fraction was obtained by crystallisation from the ether residues. A total of 10.2 g, 32% of the title compound was obtained.

Aufarbeitung

  1. temperaturereflux
  2. filtrationThe mixture was filtered hot
  3. customthe filtrate was evaporated to a yellow solid
  4. customThe solid was purified by 800 g Biotage column
  5. washeluting with 20% ethyl acetate/hexane
  6. customto give a white solid, which
  7. customwas triturated in ether
  8. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-4fc5c207ec31412a9cfec0ebd555b79e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173047B2

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