Water → HCID 9881809, Verbindung

HRID 1699736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699736
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6](I)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].O.C[N:22]([CH:24]=O)C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:24]#[N:22])[CH:5]=2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21837989Methyl 3-(hydroxymethyl)-5-iodobenzoate

Produkt 1

HCID 9881809HCID 9881809, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3.08 g of the 5-hydroxymethyl-3-iodobenzoic acid methyl ester obtained in the production example 2 was dissolved in 50 ml of dry DMF under the flow of nitrogen and then mixed with 2.32 g of the compound in the production example 3, 2.18 g of potassium carbonate and 456 mg of tetrakis(triphenylphosphine) palladium (0). The obtained mixture solution was heated and stirred at 90° C. overnight, mixed with water to stop the reaction, and then extracted with ethyl acetate. The obtained ethyl acetate layer was dried over MgSO4, and the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 2.05 g (73%) of the title compound. Colorless crystals.

Aufarbeitung

  1. temperatureThe obtained mixture solution was heated
  2. customthe reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained ethyl acetate layer was dried over MgSO4
  5. distillationthe solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2efc357a0fe549d78116f10d9575542f
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06348478B1

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