Diisobutylaluminumhydride → HCID 178441515, compound

HRID 1638561Notes

Reaction equation

HRID 1638561 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][C:11]([C:14](OC)=[O:15])=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([C:5]1[NH:6][C:7]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 178441517HCID 178441517, compound

Product 1

HCID 178441515HCID 178441515, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.1 g of 2-butyl-6-carbomethoxybenzimidazole in 50 mL of tetrahydrofuran was cooled with ice. To this solution was added dropwise 18 mL of 25% diisobutylaluminum hydride (DiBAl-H) in toluene. After the addition, the reacted mixture was stirred for 30 minutes with ice cooling and then for an additional 1 hour at room temperature. The reaction mixture was cooled back down to 0° and the reaction quenched by adding 15 mL of saturated ammonium chloride (NH4Cl) solution. The mixture was then filtered through celite and the filtrate was concentrated. The crude product was purified by silica gel column chromatography (100% EtOAc elution) to give 1.23 g of the desired product as a thick colorless oil.

Workup

  1. additionAfter the addition
  2. waitfor an additional 1 hour at room temperature
  3. temperatureThe reaction mixture was cooled back down to 0°
  4. customthe reaction quenched
  5. additionby adding 15 mL of saturated ammonium chloride (NH4Cl) solution
  6. filtrationThe mixture was then filtered through celite
  7. concentrationthe filtrate was concentrated
  8. customThe crude product was purified by silica gel column chromatography (100% EtOAc elution)

Sources & evidence

ORD record
ord-b8f234642db343f7af908cc4023066d7
Source dataset
uspto-grants-1989_11
Patent number
US04880804

Reaction notes

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