Triacetoxyperiodinane → 1-Methyl-4-phenyl-1H-imidazole-2-carboxaldehyde

HRID 537884Notes

Reaction equation

HRID 537884 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH2:13][OH:14].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 23076602(1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanol

Product 1

HCID 145989821-Methyl-4-phenyl-1H-imidazole-2-carboxaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (1-Methyl-4-phenyl-1H-imidazol-2-yl)-methanol 5 (50.0 mg, 0.266 mmol) in 1,2-dichloroethane (4.0 mL) under Ar was added Dess-Martin periodinane (124 mg, 0.292 mmol), and the mixture was stirred at room temperature for 2 hours. Saturated NaHCO3 solution was added, the organic layer was separated and the aqueous layer was extracted with 1,2-dichloroethane. The combined organic layers were dried over Na2SO4, volatiles were evaporated and the residue was purified by silica gel chromatography on a FlashMaster system (gradient elution; 0-100% ethylacetate in heptane) to afford the title compound as a white solid (39.1 mg, 79%). 1H NMR (500 MHz, DMSO-d6): δ9.76 (s, 1H), 8.11 (s, 1H), 7.84 (d, J=7.7 Hz, 2H), 7.42 (t, J=7.6 Hz, 2H), 7.30 (t, J=7.4 Hz, 1H), 3.99 (s, 3H).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with 1,2-dichloroethane
  3. dry with materialThe combined organic layers were dried over Na2SO4, volatiles
  4. customwere evaporated
  5. customthe residue was purified by silica gel chromatography on a FlashMaster system (gradient elution; 0-100% ethylacetate in heptane)

Sources & evidence

ORD record
ord-4b10aa350ee84ed484e42e045f41b6c7
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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