Sodium hydride → p-(1-Trifluoromethyl-heptyloxy)-benzonitrile

HRID 372929

Reaktionsgleichung

Reaktionsgleichung von HRID 372929
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[CH:5]([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[H][H].[Na].I[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>O.CN(C=O)C>[F:3][C:4]([F:13])([F:14])[CH:5]([O:12][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 764674-IodobenzonitrileHCID 978042-Octanol, 1,1,1-trifluoro-2×HCID 5360545SodiumHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 15724839p-(1-Trifluoromethyl-heptyloxy)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 100 ml of dry DMF containing 0.86 g of sodium hydride (purity 60%), were added dropwise 3.9 g of R-form oa 1-trifluoromethyl-heptanol, at room temperature with such a speed not causing too rapid generation of hydrogen, to prepare sodium salt (alkoxide) of R-form oa 1-trifluoromethyl-heptanol. After addition was over, stirring was continued further an hour at room temperature, followed by adding thereto 4.80 g of p-iodo-benzonitrile and then refluxing for 2 hours. After cooling, the product was introduced into iced water, and extracted with hexane. The hexane phase was washed subsequently with water, 1N-HCl aqueous solution and then water, followed by purifying with silica gel column to obtain 5.16 g of oily oa p-(1-trifluoromethyl-heptyloxy)- benzonitrile.

Aufarbeitung

  1. customat room temperature
  2. additionAfter addition
  3. waitwas continued further an hour at room temperature
  4. additionby adding
  5. temperatureAfter cooling
  6. extractionextracted with hexane
  7. washThe hexane phase was washed subsequently with water, 1N-HCl aqueous solution
  8. customby purifying with silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-2b8b5b7465ef4adc9b1eda4352119f95
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05160662

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