Potassium Carbonate → HCID 86747875, compound

HRID 1033901Notes

Reaction equation

HRID 1033901 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]CCl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[C:21](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:6]([O:18][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:7]([CH:10]=[O:11])=[C:8]([CH3:21])[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 86747875HCID 86747875, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-butylimidazol-5-aldehyde (16.92 g, 0.111 mmol, prepared by manganese dioxide oxidation of the alcohol, prepared in Example 1), chloromethyl pivalate (21.77 g, 0.145 mmol), and potassium carbonate (20.07 g, 0.145 mmol) 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 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-pivalyloxy-methylimidazole-5-aldehyde

Workup

  1. customwere removed by filtration
  2. washwashed with ether
  3. customThe combined filtrates were partitioned between 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-736bfff007ac4ad898a0e0bb39e56332
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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