Triethyl phosphonoacetate → Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate

HRID 1964149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964149
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=O)[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32].[NH4+].[Cl-]>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32]

Komponenten

6

Edukt 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672497037-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one

Produkt 1

HCID 67249397Ethyl 2-(7-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetateAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.38 mL, 6.97 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil) (279 mg, 6.97 mmol) at 0° C. The reaction mixture was stirred for 10 min, then 7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (500 mg, 2.323 mmol) in DMF (6 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h, then heated at 60° C. for 1 h, cooled down, poured into saturated NH4Cl aqueous solution, extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (361 mg). LCMS m/z=286.2 [M+H]+.

Aufarbeitung

  1. stirringstirred for 1 h
  2. temperatureheated at 60° C. for 1 h
  3. temperaturecooled down
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9ee92a99de4b40b0883976016f894de9
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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