Potassium Carbonate → 4-[[6-[3,4-Dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester

HRID 1494254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494254
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[C:11]([O:20][CH3:21])[CH:10]=1)=[O:8].[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:22][O:23][C:24](=[O:36])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]2[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[C:11]([O:20][CH3:21])[CH:10]=2)=[O:8])=[C:27]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:35]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoateHCID 149864006-Bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone

Produkt 1

HCID 149864154-[[6-[3,4-Dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl esterAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6.0 g (0.017 mol) of 6-bromo-1-[3,4-dimethoxy-5-(1-methylethyl)phenyl]-1-hexanone, 3.39 g (0.016 mol) of 2,4-dihydroxy-3-propylbenzoic acid methyl ester and 7.0 g (0.051 mol) of potassium carbonate in 120 mL of acetone and 12 mL of DMF was stirred at reflux for 19 hours. After workup as in Example 16, the crude product was purified by HPLC using 16% ethyl acetate-hexane to give 7.7 g (98% yield) of 4-[[6-[3,4-dimethoxy-5-(1-methylethyl)phenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid methyl ester as an oil. The nmr spectrum was consistent with the structure.

Aufarbeitung

  1. temperatureat reflux for 19 hours
  2. customAfter workup as in Example 16, the crude product was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3508e699b5c543b0a93b458d4e1bf3c9
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05025036

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