Potassium Carbonate → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl Ester

HRID 2117211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117211
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2C)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([O:1][C:2]2[CH:10]=[C:9]3[C:5]([C:6]([CH3:13])([CH3:14])[C:7](=[O:12])[NH:8]3)=[CH:4][CH:3]=2)[CH3:32])[CH:24]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 219317776-hydroxy-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-oneHCID 542191176-(3-Bromomethyl-phenyl)-hexanoic Acid Methyl Ester

Produkt 1

HCID 692161446-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid Methyl EsterAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 6-hydroxy-1,3,3-trimethyl-1,3-dihydro-indol-2-one (396 mg, 2.07 mmol) in DMF (7.6 mL) is added 6-(3-Bromomethyl-phenyl)-hexanoic acid methyl ester (682 mg, 2.28 mmol) and potassium carbonate (315 mg, 2.28 mmol). The resulting mixture is heated to 60° C., stirred for 2 hrs. then cooled to room temp and diluted with EtOAc. The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes) to give 352 mg of title compound. MS (ESI) 410 (M+H)+.

Aufarbeitung

  1. temperaturethen cooled to room temp
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (eluting with 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1f9c2abdb31a4f8dbda1ada84dabcb22
Quelldatensatz
uspto-grants-2008_10
Patentnummer
USRE040558E1

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