Triacetoxyperiodinane → HCID 178519856, compound

HRID 1823949Notes

Reaction equation

HRID 1823949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178519857HCID 178519857, compound

Product 1

HCID 178519856HCID 178519856, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of [2-(2-chlorophenyl)-1H-imidazol-4-yl]methanol (1.0 g, 4.81 mmol) in CH2Cl2 (50 mL) at to 25° C. is added sodium bicarbonate (1.21 g, 14.4 mmol) followed by Dess-Martin periodinane (2.29 g, 5.29 mmol). The reaction mixture is then stirred at to 25° C. for 1 hour. Subsequently, the reaction mixture is poured into a separatory funnel, diluted with CH2Cl2 and washed with a saturated sodium sulfite solution. The organic layer is dried over sodium sulfate and concentrated. The crude product is purified by column chromatography (50% ethyl acetate in hexanes) to afford 182 mg of 2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde.

Workup

  1. additionSubsequently, the reaction mixture is poured into a separatory funnel
  2. washwashed with a saturated sodium sulfite solution
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f0f6afa64f9c4705a13a97e1c338e1b3
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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