Iodoethane → 5-(3-Ethoxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

HRID 2171152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171152
[OH:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH2:28](I)[CH3:29]>C(#N)C>[CH2:28]([O:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH3:29]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Produkt 1

HCID 674672705-(3-Ethoxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-oneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirring solution of 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one (80 mg, 0.279 mmol) in acetonitrile (10 mL) was added potassium carbonate (115 mg, 0.837 mmol) and ethyl iodide (130 mg, 0.837 mmol) and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether) to afford the title compound as a solid (50 mg, 57%).

Aufarbeitung

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-e52f6263338f4e48b2b6fa252af14390
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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