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

HRID 8895

Reaktionsgleichung

Reaktionsgleichung von HRID 8895
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-edc697d54b1148c0900b356e7c803263
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091222B2

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