Ammonium Chloride → 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

HRID 350015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350015
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[CH2:20]([N:27]1[CH:31]=[C:30]([CH:32]=O)[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C(COC)OC.CO>[CH2:20]([N:27]1[CH:31]=[C:30]([CH2:32][C:10]#[N:11])[C:29]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 693145121-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrileAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel3×

Versuchsvorschrift

A solution of p-toluenesufonylmethylisocyanide (10.3 g) in dimethoxyethane (50 ml) was added to a mixture of potassium t-butoxide (11.2 g) and dimethoxyethane (50 ml) at −78° C., and the mixture was stirred for 5 minutes. A solution of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (14.6 g) in dimethoxyethane (50 ml) was added to the mixture. After stirring at the same temperature for 1 hour, the mixture was stirred for 1 hour while raising the temperature. Methanol (150 ml) was added to the mixture, which was refluxed for 1 hour. After cooling, the reaction solution was poured into saturated aqueous ammonium chloride solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.1 g, yield 86%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).

Aufarbeitung

  1. stirringAfter stirring at the same temperature for 1 hour
  2. stirringthe mixture was stirred for 1 hour
  3. temperaturewhile raising the temperature
  4. temperaturewas refluxed for 1 hour
  5. temperatureAfter cooling
  6. extractionwas extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-65956e39d6714037a78b49badad82e15
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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