1-Bromo-2-methylpropane → 5-(3-Isobutoxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

HRID 2171154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171154
[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)[CH:29]([CH3:31])[CH3:30]>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])[CH:29]([CH3:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 674677565-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one

Produkt 1

HCID 674667945-(3-Isobutoxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-oneAusbeute 31,4 %

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 isobutyl bromide (115 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, 31.4%).

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-b73ae8ad20c74f9996bede988430281e
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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