Phenol → HCID 9909232, Verbindung

HRID 1637200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637200
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[O:7]([C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 11046271HCID 11046271, Verbindung

Produkt 1

HCID 9909232HCID 9909232, VerbindungAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Phenol (108 mg, 1.15 mmol) was added to a stirred suspension of sodium hydride (46 mg of 60% dispersion in mineral oil, 1.15 mmol) in anhydrous dimethylformamide (1 ml), under a nitrogen atmosphere. Ethyl 3-chloro-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Preparation 4, 200 mg, 0.58 mmol) was added to the mixture after 30 minutes, and the mixture was then heated to 75° C. for 48 hours. The reaction was partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using diethyl ether as eluant. The isolated product was crystallised from hexane to give the title compound as a colourless solid (40 mg).

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel
  7. customThe isolated product was crystallised from hexane

Quellen und Nachweise

ORD-Eintrag
ord-184108eb7b4e4b9dbc1139184ebfd988
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040309

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