Potassium Carbonate → HCID 14330011, Verbindung

HRID 2164950

Reaktionsgleichung

Reaktionsgleichung von HRID 2164950
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[C:12]([OH:19])[C:11]=1[CH2:20][CH2:21][CH3:22].[S:24]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33]OS(=O)(=O)C)(=[O:27])(=[O:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[C:12]([O:19][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][S:24]([CH3:25])(=[O:27])=[O:26])[C:11]=1[CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 147571Diethylene Glycol DimethanesulfonateHCID 14330007Methyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexanoate

Produkt 1

HCID 14330011HCID 14330011, VerbindungAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4.0 g (0.012 mole) of 6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexanoic acid methyl ester, 16.3 g (0.062 mole) of diethyleneglycol dimesylate and 3.4 g (0.024 mole) of anhydrous potassium carbonate in 90 ml of anhydrous acetone and 4 ml of anhydrous dimethylformamide was stirred at reflux for 22 hours. The solvents were removed in vacuo and the residue was treated with 100 ml of 50% ethyl acetate-hexane. Some of the residual starting dimesylate was insoluble and was removed by filtration. The filtrate was concentrated in vacuo and the residual oil was purified by HPLC to give 4.8 g (80% yield) of 6-[4-acetyl-3-[2-[2-[(methylsulfonyl)oxy]ethoxy]ethoxy]-2-propylphenoxy]hexanoic acid methyl ester as an oil.

Aufarbeitung

  1. temperatureat reflux for 22 hours
  2. customThe solvents were removed in vacuo
  3. additionthe residue was treated with 100 ml of 50% ethyl acetate-hexane
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residual oil was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d5ae3efa277b499f9d06dc135a3872c3
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04507498

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