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

HRID 1613080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613080
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-24774a4368774572975421f85b4dab6b
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05191108

Notizen zur Reaktion

Wird geladen…