Sodium Methoxide → HCID 15840670, Verbindung

HRID 342756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342756
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12](=O)N(C)C)=[C:7]([Cl:17])[CH:6]=1.C[O-].[Na+].BrC[CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([C:31]([CH2:41][CH3:42])=[CH:32][C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1>CO>[Cl:17][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:18])[CH:10]=[CH:9][C:8]=1[S:11][CH2:12][CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([C:31]([CH2:41][CH3:42])=[CH:32][C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 10942334Sodium MethoxideHCID 15840682HCID 15840682, VerbindungHCID 15840683HCID 15840683, Verbindung

Produkt 1

HCID 15840670HCID 15840670, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 3-chloro-4-dimethylcarbamoylthiophenylacetic acid methyl ester (129 mg, 0.3991 mmol) in 0.75 mL methanol was added a 0.5M solution of sodium methoxide in methanol. This mixture was heated to 70° C. for 90 minutes. After cooling to ambient temperature, a solution of 7-(3-bromopropoxy)-4-ethyl-8-propylcoumarin (Step D) in 1.2 mL methanol was added dropwise. The mixture was heated to 70° C. for 16 hours. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic mixture was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to provide the title compound.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. temperatureThe mixture was heated to 70° C. for 16 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic mixture was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e0bbc9eb68214549a283e6f6a681b57e
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859051

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