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

HRID 515662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515662
[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-3ae9cd7654fd42698c3f1010b5ad1c65
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108969B2

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