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

HRID 1416342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416342
[CH2:1]([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]O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:54]C(Cl)(Cl)Cl>C(#N)C>[CH2:1]([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:54])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 70117020Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol prepared in the previous stage was dissolved in acetonitrile (400 ml). Triphenyl phosphine (103.5 g, 0.4 mol) and tetrachloromethane (120 g, 0.79 mol) were added and the mixture was refluxed for 2 hours. Then the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in methanol (160 ml) and water (40 ml) and extracted three times with petroleum ether (3×200 ml) at boiling point. Petroleum ether layers were combined and evaporated to dryness under reduced pressure. The residue was crystallized twice from ethanol (700 ml). Yield 36 g.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThen the mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (160 ml)
  4. extractionwater (40 ml) and extracted three times with petroleum ether (3×200 ml)
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was crystallized twice from ethanol (700 ml)

Quellen und Nachweise

ORD-Eintrag
ord-ffe92b3c886043e3b97683b645bd4fba
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05912273

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