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4-Iodobenzonitrile → 4-[2-(1-trityl-1H-imidazol-4-ylmethoxy)acetyl]benzonitrile

HRID 1095301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1095301
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].CON(C)[C:18](=[O:46])[CH2:19][O:20][CH2:21][C:22]1[N:23]=[CH:24][N:25]([C:27](C2C=CC=CC=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)C2C=CC=CC=2)[CH:26]=1>O1CCCC1>[C:27]([N:25]1[CH:26]=[C:22]([CH2:21][O:20][CH2:19][C:18]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[O:46])[N:23]=[CH:24]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:10]1[CH:12]=[CH:26][CH:22]=[CH:21][CH:11]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 764674-IodobenzonitrileHCID 86632953N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamideHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 667823264-[2-(1-trityl-1H-imidazol-4-ylmethoxy)acetyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of 14 mmol of 4-iodobenzonitrile [3058-39-7] in 20 ml of tetrahydrofuran is cooled to −30° C., and 14.80 mmol of i-propylmagnesium chloride (2M in tetrahydrofuran) are added. The mixture is stirred at −30° C. for 60 minutes and a solution, precooled to −30° C., of 10.0 mmol of N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamide in 30 ml of tetrahydrofuran is added. The mixture is stirred at −30° C. for 30 minutes, and then the reaction mixture is warmed to room temperature and quenched with saturated aqueous ammonium chloride solution. The phases are separated, and the aqueous phase is extracted with ethyl acetate (3×). The combined organic phases are washed with brine, dried with magnesium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60 F).

Aufarbeitung

  1. additionis added
  2. stirringThe mixture is stirred at −30° C. for 30 minutes
  3. temperaturethe reaction mixture is warmed to room temperature
  4. customquenched with saturated aqueous ammonium chloride solution
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate (3×)
  7. washThe combined organic phases are washed with brine
  8. dry with materialdried with magnesium sulphate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7a379bb01a704fa6a3c3b18e5063e3ca
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138176B2

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