1-Bromopropane → 5-(2,4-Dimethoxy-3-propoxy-phenyl)-3H-isobenzofuran-1-one

HRID 2171153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171153
[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](Br)[CH2:29][CH3:30]>C(#N)C>[CH3:21][O:20][C:3]1[C:2]([O:1][CH2:28][CH2:29][CH3:30])=[C:7]([O:8][CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[O:14][CH2:13]2

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Produkt 1

HCID 674630045-(2,4-Dimethoxy-3-propoxy-phenyl)-3H-isobenzofuran-1-oneAusbeute 32,8 %

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 propyl bromide (103 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 (30 mg, 32.8%).

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-08b707ccfc564fd2bb4b45c8f590c406
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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