Ethyl Acetate → HCID 19906362, Verbindung

HRID 2371808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371808
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][C:12]2=[O:15])=[CH:8][CH:7]=1)=[O:4].C(OCC)(=O)C>[Pd].CN(C)C=O>[OH:15][CH:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:16])([F:17])[F:1])[CH:14]=2)[CH2:10][CH2:11]1

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 19906408HCID 19906408, Verbindung

Produkt 1

HCID 19906362HCID 19906362, VerbindungAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 10% (w/w) palladium on carbon (2.34 g), 6-(trifluoroacetamido)indan-1-one (7.79 g), ethyl acetate (53 ml) and dimethylformamide (11 ml) was hydrogenated at atmospheric pressure for 72 h. The reaction mixture was filtered through diatomaceous earth with ethyl acetate wash and evaporated. The residue was flash chromatographed, eluting with 95:5 methylene chloride:methanol, and triturated with ether to give 1-hydroxy-6-(trifluoroacetamido)indane (4.41 g, 56%) as a colorless solid; mp 123.0°-124.5° C.; MS(EI), m/e=245(M+.).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through diatomaceous earth with ethyl acetate
  2. washwash
  3. customevaporated
  4. customchromatographed
  5. washeluting with 95:5 methylene chloride
  6. custommethanol, and triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-28712b2f986e4d909e9c82d8aab31a17
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05095038

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