4-Iodobenzonitrile → 4-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)benzonitrile

HRID 1712911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712911
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[C:15]([N:34]1[CH:38]=[C:37]([CH:39]=[O:40])[N:36]=[CH:35]1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[OH:40][CH:39]([C:37]1[N:36]=[CH:35][N:34]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:38]=1)[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 764674-IodobenzonitrileHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 154357104-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of 14.80 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 11.84 mmol of 1-trityl-1H-imidazole-4-carbaldehyde [33016-47-6] 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 obtained as a white solid from the residue by recrystallization from ethyl acetate. Rf=0.23 (CH2Cl2-2M NH3 in EtOH 97:3); Rt=7.32.

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-a406b1aa5cbc4da287804452d0024b9e
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795253B2

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