Potassium Carbonate → 1-cyclopropyl-4-ethynyl-2,5-dimethyl-1H-imidazole

HRID 8895

Reaction equation

HRID 8895 reaction equation
COP(=O)OC.[C:7](=O)([O-])[O-].[K+].[K+].[CH:13]1([N:16]2[C:20]([CH3:21])=[C:19]([CH:22]=O)[N:18]=[C:17]2[CH3:24])[CH2:15][CH2:14]1>CO>[CH:13]1([N:16]2[C:20]([CH3:21])=[C:19]([C:22]#[CH:7])[N:18]=[C:17]2[CH3:24])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13361Phosphonic acid, dimethyl esterHCID 219853871-Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 219853851-cyclopropyl-4-ethynyl-2,5-dimethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (0.6 g, 3 mmol) was dissolved in 10 mL of methanol. Potassium carbonate (0.74 g, 5 mmol) was added. A solution of 1-Cyclopropyl-2,5-dimethyl-1H-imidazole-4-carbaldehyde (0.42 g, 3 mmol) in 5 ml methanol was added drop wise at room temperature. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 15 mL water and extracted three times with ethyl acetate (15 ml each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 80:20→0:100 gradient) and the desired compound was obtained as a white solid (0.12 g, 30%), MS: m/e=161.4 (M+).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (15 ml each)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 80:20→0:100 gradient)

Sources & evidence

ORD record
ord-edc697d54b1148c0900b356e7c803263
Source dataset
uspto-grants-2006_08
Patent number
US07091222B2

Linked notes

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