N-benzimidazolyl-1,2-propanediol → (1H-Benzimidazol-1-yl)acetaldehyde

HRID 983610

Reaction equation

HRID 983610 reaction equation
[N:1]1([CH:10](O)[CH:11]([OH:13])C)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I([O-])(=O)(=O)=O.[Na+]>O>[N:1]1([CH2:10][CH:11]=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 22018573N-benzimidazolyl-1,2-propanediolHCID 23667635Sodium periodate

Product 1

HCID 22018662(1H-Benzimidazol-1-yl)acetaldehydeYield 41.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The intermediate, N-benzimidazolyl-1,2-propanediol (0.66 g 3.4 mmol) from above was dissolved in water (25 mL) and treated with sodium periodate (0.88 g, 4.1 mmol) with stirring for 1.5 hours. The solution was then extracted with dichloromethane, dried (MgSO4), filtered and concentrated to yield 2-(benzimidazol-1-yl)-ethanal (0.22 g, 1.4 mmol) which was used immediately without further purification in the next reaction.

Workup

  1. extractionThe solution was then extracted with dichloromethane
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b635bb375f34dfa9917c766faca0302
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Linked notes

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