Potassium Carbonate → 2-n-Butyl-1-pivalyloxymethylimidazole-5-aldehyde

HRID 2081860Notes

Reaction equation

HRID 2081860 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:10]=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[C:12]([O:18][CH2:19]Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:6]([CH2:19][O:18][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:7]([CH:10]=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 27356712-Butyl-5-formylimidazole

Product 1

HCID 193873272-n-Butyl-1-pivalyloxymethylimidazole-5-aldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-butylimidazol-5-aldehyde (16,92 g, 0.111 mol, prepared by manganese dioxide oxidation of the alcohol, prepared in Example 1, Method 2), chloromethyl pivalate (21.77 g, 0.145 mol), and potassium carbonate (20.07 g, 0.145 mol) in 200 ml of dimethylformamide was stirred at ambient temperature under argon for four days. The solids were removed by filtration and washed with ether. The combined filtrates were partitioned between diethyl ether and water. The ether phase was washed successively with water and brine, dried over magnesium sulfate and concentrated under vacuum to give 23.6 g of 2-n-butyl-1-pivalyloxymethylimidazole-5-aldehyde.

Workup

  1. customThe solids were removed by filtration
  2. washwashed with ether
  3. customThe combined filtrates were partitioned between diethyl ether and water
  4. washThe ether phase was washed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f0eb4801b6eb4dad93ee8cfc6bab91e5
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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