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Ethanol → HCID 178442568, Verbindung

HRID 1770177
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1770177
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:21]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]2[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[CH2:22][CH2:23][CH2:24][CH3:25].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:35]3[CH:34]=[CH:33][C:32]([C@H:29]4[CH2:30][CH2:31][C@H:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28]4)=[CH:37][CH:36]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 220990862-Octylindane-5-boronic acidHCID 178444243HCID 178444243, Verbindung

Produkt 1

HCID 178442568HCID 178442568, VerbindungAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 241BenzeneLösungsmittel

Versuchsvorschrift

1.78 g (6.5 mM) of 2-octylindan-5-boronic acid, 2.0 g (6.5 mM) of 4-(trans-4-pentylcyclohexy)phenyl bromide, 4 ml of ethanol, 8 ml of benzene, 8 ml of 2M-sodium carbonate aqueous solution and 0.24 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 5 hours under stirring. After the reaction, the reaction mixture was poured into ice water, followed by extraction with toluene, washing with water and drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: hexane) and recrystallized from a mixture solvent (toluene/methanol) to obtain 1.52 g of 2-octyl-5-[4-(trans-4-pentylcyclohexyl)phenyl]indan (Yield: 51.0%). ##STR310##

Aufarbeitung

  1. temperatureheat-refluxed for 5 hours
  2. customAfter the reaction
  3. extractionfollowed by extraction with toluene
  4. washwashing with water
  5. dry with materialdrying with anhydrous sodium sulfate
  6. customThen, the sodium sulfate was removed from the mixture
  7. customthe resultant mixture was evaporated
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane)
  10. customrecrystallized from a mixture solvent (toluene/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-7a009d87c54740418c3775e8eb6d4111
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05385692

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