z-1-[4-(2-Benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene → Ospemifene

HRID 1416343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416343
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:19](\[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)/[CH2:20][CH2:21][Cl:22])=[CH:14][CH:13]=1)C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:22][CH2:21][CH2:20]/[C:19](/[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[C:18](/[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:17][CH:16]=1)\[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

5

Edukt 1

HCID 70116950z-1-[4-(2-Benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene

Produkt 1

HCID 3036505Ospemifene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Z-1-[4-(2-benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene (36 g, 0.08 mol) was dissolved in the mixture of ethyl acetate (350 ml) and ethanol (350 ml). Palladium on carbon (5%, 0.28 g) was added and the solution was flushed with hydrogen gas until there was not any starting compound left (thin layer chromatography). Palladium on carbon was filtered off through siliceous earth and the filtrate was evaporated. The residue was crystallized from the mixture of ethanol (155 ml) and water (65 ml). Yield 20 g.

Aufarbeitung

  1. customthe solution was flushed with hydrogen gas until there
  2. waitleft (thin layer chromatography)
  3. filtrationPalladium on carbon was filtered off through siliceous earth
  4. customthe filtrate was evaporated
  5. customThe residue was crystallized from the mixture of ethanol (155 ml) and water (65 ml)

Quellen und Nachweise

ORD-Eintrag
ord-cf2d751911fd45c1a6d99deb14d0f845
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912273

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