tert-Butyl (triphenylphosphoranylidene) acetate → tert-Butyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetate

HRID 1964080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964080
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C:20](=O)[C:13]3=[CH:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C:20](=[CH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:13]3=[CH:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 216859796-Phenylmethoxy-1,2-dihydropyrrolo[1,2-a]indol-3-one

Produkt 1

HCID 67250801tert-Butyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ylidene)acetateAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

7-(Benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (3.6 g, 12.98 mmol) and (tert-butoxycarbonylmethylene)triphenylphosphorane (5.86 g, 15.58 mmol) were dissolved in toluene (40 mL) and the reaction mixture was heated under reflux and stirred for 24 h. The solution was cooled to room temperature. The precipitate was collected by filtration. The filtrate was concentrated under reduced pressure to yield additional white solid. The process was repeated to provide the title compound (1.391 g). LCMS m/z=376.4 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux
  3. filtrationThe precipitate was collected by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield additional white solid

Quellen und Nachweise

ORD-Eintrag
ord-adb810e46f054a58b78406f5ccd24b97
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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