Ethyl Acetate → HCID 178494189, compound

HRID 2377969Notes

Reaction equation

HRID 2377969 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]([C:8]2[C:9](=[O:15])[NH:10][CH:11]=[CH:12][C:13]=2[I:14])=[N:5][C:4]=1[CH3:16].[CH3:17]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>ClCCl>[I:14][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([O:15][CH3:17])[C:8]=1[C:6]1[NH:7][C:3]([CH:2]=[O:1])=[C:4]([CH3:16])[N:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 178432606HCID 178432606, compound

Product 1

HCID 178494189HCID 178494189, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-(5-(hydroxymethyl)-4-methyl-1H-imidazol-2-yl)-4-iodopyridin-2(1H)-one (0.020 g, 0.0579 mmol) in dichloromethane (2 mL) was added the Dess-Martin reagent (0.049 g, 0.1158 mmol) at room temperature. The reaction became clear after 5 minutes of stirring. Ethyl acetate was added and the reaction was washed with 5% aqueous Na2S2O3.5H2O, saturated aqueous sodium bicarbonate and brine. The organic layer was driede over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on silica gel chromatography (ethyl acetate) to give the title material (0.009 g, 45%). 1H NMR (400 MHz, Acetone-d6) δ (ppm): 2.47 (s, 3H) 3.72 (s, 3H) 7.42-7.50 (m, 1H) 7.78 (s, 1H) 9.81 (s, 1H).

Workup

  1. washthe reaction was washed with 5% aqueous Na2S2O3.5H2O, saturated aqueous sodium bicarbonate and brine
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6d602de9fadd49b9b56df4f9e17bf8a5
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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