Sodium Thiosulfate → ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate

HRID 2368479Notes

Reaction equation

HRID 2368479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][OH:19])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH:18]=[O:19])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71117501ethyl 1-(4-fluorophenyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxylate

Product 1

HCID 86677543ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 1-(4-fluorophenyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxylate (15) (210 mg, 0.80 mmol), and Dess-Martin Periodinane (DMP) (562 mg, 1.32 mmol) in dichloromethane (8 mL) was stirred at room temperature for 1 h. The reaction was added to a 1:1 mixture of Na2S2O3 (10% aq.) and NaHCO3 (sat.), then extracted with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes) to give ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate (16).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b472468dcc624edbad31ddb23b39f60c
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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