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

HRID 36992

Reaction equation

HRID 36992 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 vaccum 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 vaccum

Sources & evidence

ORD record
ord-826ff577303045ea8be54312b21db837
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Linked notes

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