Réaction #1861072

Équation de réaction

1-trityl-imidazole-4-carboxaldehyde

phenylmagnesium bromide

NH4Cl

→

4-benzyl-1H-imidazole

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous phase is extracted three times with CH2Cl2
2. 2
   SéchageThe organic phase is dried over magnesium sulphate
3. 3
   Filtrationfiltered
4. 4
   Autrethe solvent is removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue is dissolved in concentrated HI solution (75 mL)
6. 6
   Températurethe reaction mixture is heated
7. 7
   Températureat reflux overnight
8. 8
   TempératureAfter cooling at room temperature
9. 9
   Extractionthe reaction mixture is extracted three times with Et2O
10. 10
    workup.ADDITIONby adding solid Na2CO3 to pH 7, solid NaHSO3
11. 11
    workup.ADDITIONis added until the red colour
12. 12
    Extractionthe aqueous phase is extracted three times with Et2O
13. 13
    SéchageThe organic phase is dried over magnesium sulphate
14. 14
    Filtrationfiltered
15. 15
    Autrethe solvent is removed under reduced pressure

Mode opératoire

To a solution of 1-trityl-imidazole-4-carboxaldehyde (5 g, 14.8 mmoles) in THF (40 mL) is added dropwise a solution of 1M phenylmagnesium bromide in THF (17.7 mL, 17.7 mmoles). The reaction mixture is stirred at room temperature for 3 h, then it is poured into a saturated solution of NH4Cl. The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is dissolved in concentrated HI solution (75 mL) and the reaction mixture is heated at reflux overnight. After cooling at room temperature, the reaction mixture is extracted three times with Et2O. The aqueous phase is basified by adding solid Na2CO3 to pH 7, solid NaHSO3 is added until the red colour disappeared and the aqueous phase is extracted three times with Et2O. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure to give 4-benzyl-1H-imidazole.

Source