Triacetoxyperiodinane → 1H-Benzimidazole-2-carboxaldehyde,5-chloro-1-methyl-(9CI)

HRID 858620Notes

Reaction equation

HRID 858620 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH3:11])[C:7]([CH2:9][OH:10])=[N:8][C:4]=2[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH3:11])[C:7]([CH:9]=[O:10])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 4066944HCID 4066944, compound

Product 1

HCID 450780571H-Benzimidazole-2-carboxaldehyde,5-chloro-1-methyl-(9CI)Yield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5-chloro-1-methyl-1H-benzimidazol-2-yl)methanol (1.5 g, 7.7 mmol) dissolved in CH2Cl2 at room temperature was treated with Dess-Martin periodinane (4.9 g, 11.5 mmol). The reaction was stirred for 15 hours before the solvent was removed. The residue was purified by flash column chromatography (0–3% MeOH in CH2Cl2) to give the product (1.0 g, 66% yield). 1H NMR (300 MHz, CDCl3) δ: 4.16 (s, 3 H), 7.40–7.47 (m, 2 H), 7.90–7.93 (m, 1 H), 10.11 (s, 1 H).

Workup

  1. customwas removed
  2. customThe residue was purified by flash column chromatography (0–3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9d4727fceb1443c18da88604011ad423
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…