Diisobutylaluminumhydride → HCID 86649913, compound

HRID 1803157Notes

Reaction equation

HRID 1803157 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]1[CH:26]=[C:25]([C:27](OCC)=[O:28])[N:24]=[CH:23]1>>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]1[CH:26]=[C:25]([CH:27]=[O:28])[N:24]=[CH:23]1

Participants

3

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66858320HCID 66858320, compound

Product 1

HCID 86649913HCID 86649913, compoundYield 59%

Procedure

Step N (2): Diisobutylaluminum hydride (1 M in toluene, 17.2 mL, 17.1 mmol) was added to a −78° C. solution of ethyl 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carboxylate (2.0 g, 6.9 mmol). After 30 min, the reaction mixture was quenched with 1 N HCl. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified using silica gel column chromatography (EtOAc/hexane) to afford 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carbaldehyde (1.0 g, 59% yield).

Workup

  1. customthe reaction mixture was quenched with 1 N HCl
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified

Sources & evidence

ORD record
ord-7b8120083e8a4af2b464dc671a841536
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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