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

HRID 8895

反応式

HRID 8895 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-edc697d54b1148c0900b356e7c803263
出典データセット
uspto-grants-2006_08
特許番号
US07091222B2

関連ノート

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