Hexane → HCID 21973146, Verbindung

HRID 1814825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814825
[Cl-:1].[NH4+:2].C[Al](C)C.CCCCCC.[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][CH3:31])=[C:25]([CH:28]=1)[C:26]#[N:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.ClCCl>[ClH:1].[CH2:13]([O:20][C:21]1[CH:28]=[C:25]([C:24]([O:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)[C:26]([NH2:2])=[NH:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 219731695-Benzyloxy-2-ethoxybenzonitrile

Produkt 1

HCID 21973146HCID 21973146, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0-5° C. Trimethylaluminum is added dropwise as a 2M solution in hexane (445 ml, 888.3 mmol), and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitrile (100 g, 394.8 mmol) (example 32A) is added, and the mixture is stirred at 80° C. overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 200 g of silica gel and 2 l of dichloromethane, and the mixture is stirred for 30 min. The mixture is filtered off with suction and the filter cake is washed with methanol. The organic phases are combined and concentrated. The resulting residue is triturated using a mixture of dichloromethane/methanol 9:1, filtered and concentrated using a rotary evaporator. The residue is then triturated with ether, and the colorless solid is filtered off with suction.

Aufarbeitung

  1. stirringthe mixture is stirred at 80° C. overnight
  2. customThe cooled reaction mixture
  3. temperaturecooling
  4. stirringthe mixture is stirred for 30 min
  5. filtrationThe mixture is filtered off with suction
  6. washthe filter cake is washed with methanol
  7. concentrationconcentrated
  8. customThe resulting residue is triturated
  9. additiona mixture of dichloromethane/methanol 9:1
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customa rotary evaporator
  13. customThe residue is then triturated with ether
  14. filtrationthe colorless solid is filtered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-d58d186105994bd6961aacecc5b80d80
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878708B2

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