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

HRID 2399242Notes

Reaction equation

HRID 2399242 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>[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

5

Reactant 3

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

Product 1

HCID 193873272-n-Butyl-1-pivalyloxymethylimidazole-5-aldehydeYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-butylimidazol-5-aldehyde (16.9 g, 0.111 mol), chloromethyl pivalate (21.77 g, 0.145 mol), and potassium carbonate (20.07 g, 0.145) in 200 ml of dimethylformamide was stirred at ambient temperature under argon for four days. The solids were removed by filteration 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-pivalyloxymethylimidazol-5-carboxaldehyde.

Workup

  1. customThe solids were removed by filteration
  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-375e2659c8af44a197ca1d1e4eededf7
Source dataset
uspto-grants-1995_09
Patent number
US05447949

Reaction notes

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