Hydrochloric Acid → HCID 11208635, Verbindung

HRID 1386613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386613
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[C:28](=[O:30])[CH3:29].Cl>O1CCCC1.CCCCCC.C(OCC)C.C(OCC)(=O)C.O>[C:28]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)(=[O:30])[CH3:29]

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 6187104-Bromo-4'-heptylbiphenylHCID 178418339Butyllithium

Produkt 1

HCID 11208635HCID 11208635, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a solution of 4-bromo-4′-n-heptylbiphenyl (5.1 g) in tetrahydrofuran (60 ml) was added a solution of #n-butyllithium in a mixture of n-hexane and diethyl ether (1.6M, 9.7 ml) at −60° C. After stirring at −60° C. for 30 minutes, to the mixture was added N,N-dimethylacetamide (4.3 ml) and the reaction mixture was allowed to warm to 0° C. The reaction mixture was taken up into a mixture of cold water and ethyl acetate, and the pH was adjusted to around 1 with 1N hydrochloric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (150 ml) eluting with a mixture of n-hexane and ethyl acetate (20:1, V/V) to give 4-Acetyl-4′-n-heptylbiphenyl (1.60 g).

Aufarbeitung

  1. temperatureto warm to 0° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (150 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (20:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-a65ec7d1417f4ad79f30cd659d43a306
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265536B1

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