Ammonium Chloride → N-(3-cyclohexylphenyl)-4-hydroxy-3-methoxyphenylacetamide

HRID 7061

Reaktionsgleichung

Reaktionsgleichung von HRID 7061
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[Br-].[CH:22]1([Zn+])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>O1CCCC1.[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>[CH:22]1([C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:19][CH3:20])[CH:4]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 120966604-hydroxy-N-(3-iodophenyl)-3-methoxyphenylacetamideHCID 178418970HCID 178418970, Verbindung

Produkt 1

HCID 9881043N-(3-cyclohexylphenyl)-4-hydroxy-3-methoxyphenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Intermediate 1 (850 mg) and tetrakis(triphenylphosphine)-palladium (0) (250 mg) are dissolved in tetrahydrofuran (16 ml), and thereto is added a 0.5 M tetrahydrofuran solution (20 ml) of cyclohexylzinc bromide under argon atmosphere at room temperature, and the mixture is stirred for 18 hours. A saturated aqueous ammonium chloride solution is added to the reaction solution, and the mixture is extracted with ethyl acetate. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (120 mg).

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b59d64d91f264abeae1d4d6a9e60e2b0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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