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2-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

HRID 2383370
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Reaktionsgleichung

Reaktionsgleichung von HRID 2383370
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:6][CH:5]=1>C(OCC)(=O)C.[Cl-].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.[Rh+3].[Cl-].[Cl-]>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])=[CH:8][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

Produkt 1

HCID 591459612-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dioneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21948325Rhodium tris(triphenylphosphine)chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-{2-[4-(2-hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione (Preparation 9, 62.0 g, 211.37 mmol) was dissolved in ethyl acetate (1200 mL). To this was added rhodium tris(triphenylphosphine)chloride, (12.7 g, 13.7 mmol) and the mixture hydrogenated at 20 psi, room temperature for 24 hours. The reaction was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate (1000 mL) and passed through a pad of silica gel, washing with ethyl acetate. The solvent was removed in vacuo to yield a light brown solid which was recrystallised from ethyl acetate:heptane (4:1, by volume) to yield the title compound as an off-white crystalline solid, in 85% yield, 53 g,

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (1000 mL)
  4. washwashing with ethyl acetate
  5. customThe solvent was removed in vacuo
  6. customto yield a light brown solid which
  7. customwas recrystallised from ethyl acetate:heptane (4:1, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-b7e86227c30a42d1873dac977e6ca476
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263623B2

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