Sodium Hydroxide → HCID 19815283, compound

HRID 653921Notes

Reaction equation

HRID 653921 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[C:11]([Cl:15])[N:10]=[C:9]2[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:5][CH:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.[OH-:32].[Na+]>C1C=CC=CC=1>[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[C:11]([Cl:15])[N:10]=[C:9]2[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:5][CH:4]=1)=[O:32]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19815325HCID 19815325, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19815283HCID 19815283, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5.05 g of 1-(4-cyanobenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole in 350 mL of benzene at 25° was added dropwise 22.8 mL of diisobutylaluminum hydride (0.15 M in toluene). The mixture was warmed to 45° and stirred for 16 hours. After cooling, the reaction mixture was poured in ice-cold 20% aqueous sulfuric acid. This solution was allowed to warm to 25° and then stirred for 2 hours. The solution was cooled to 0°, neutralized using aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% ethyl acetate/benzene) provided 3.60 g of 1-(4-formyl-benzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole; NMR (200 MHz, CDCl3) δ: 9.96 (s, 1H); 7.47 (A2M2, 4H); 5.26 (s, 2H); 4.42 (s, 2H); 2.54 (t, 2H); 1.64 (quint., 2H); 1.32 (sext., 2H); 0.86 (t, 3H).

Workup

  1. temperatureThe mixture was warmed to 45°
  2. temperatureAfter cooling
  3. temperatureto warm to 25°
  4. stirringstirred for 2 hours
  5. temperatureThe solution was cooled to 0°
  6. extractionextracted with ethyl acetate
  7. washThe combined organic phases were washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2a30290420bf470f99a0c7d38b552ff6
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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