2-n-Butyl-5-hydroxymethyl-4-iodoimidazole → 2-Butyl-5-formyl-4-iodo-imidazole

HRID 1955735Notes

Reaction equation

HRID 1955735 reaction equation
[N+]([O-])([O-])=O.[Ce].[NH4+].[CH2:7]([C:11]1[NH:12][C:13]([CH2:17][OH:18])=[C:14]([I:16])[N:15]=1)[CH2:8][CH2:9][CH3:10]>O.C(OCC)(=O)C>[CH2:7]([C:11]1[NH:12][C:13]([CH:17]=[O:18])=[C:14]([I:16])[N:15]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 148985472-n-Butyl-5-hydroxymethyl-4-iodoimidazoleHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 1784182622-Butyl-5-formyl-4-iodo-imidazoleYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ammonium cerium nitrate (125 g; 228 mmol) in water (320 ml) was added to a solution of Example 28 (42 g crude; 95 mmol) in ethyl acetate (90 ml) and the mixture was stirred overnight. The aqueous phase was extracted three times with ethyl acetate, then rendered alkaline with NaHCO3 and extracted again with ethyl acetate. The combined organic phases were washed with 5% strength NaHCO3 solution and saturated sodium chloride solution, dried and concentrated. Silica gel chromatography of the residue (hexane/ethyl acetate step gradient) gave 19.2 g of a yellow solid [72% of theory; m.p. 80°-5° C.; Rf : 0.54 (methylene chloride: methanol=10:1)].

Workup

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. extractionextracted again with ethyl acetate
  3. washThe combined organic phases were washed with 5% strength NaHCO3 solution and saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5110ccf2c01a4e248988a60b4f9b9779
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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