Potassium Carbonate → 4-Ethynyl-1-(4-fluorophenyl)-2-methyl-1H-imidazole

HRID 491335

反応式

HRID 491335 の反応式
COP(=O)OC.[C:7](=O)([O-])[O-].[K+].[K+].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([CH:25]=O)[N:22]=[C:21]2[CH3:27])=[CH:16][CH:15]=1>CO>[C:25]([C:23]1[N:22]=[C:21]([CH3:27])[N:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH:24]=1)#[CH:7]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 13361Phosphonic acid, dimethyl esterHCID 859979931-(4-fluoro-phenyl)-2-methyl-1H-imidazole-4-carbaldehyde

生成物 1

HCID 116655954-Ethynyl-1-(4-fluorophenyl)-2-methyl-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 (6.51 g, 33.9 mmol) was dissolved in 100 mL methanol. Potassium carbonate (7.81 g, 56.5 mmol) was added. A solution of 1-(4-fluoro-phenyl)-2-methyl-1H-imidazole-4-carbaldehyde (5.77 g, 45 mmol) in 100 mmol methanol was added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 150 mL water and extracted three times with ethyl acetate (150 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 100:0->0:100 gradient) and the desired compound was obtained as a white solid (3.81 g, 67%), MS: m/e=200.1 (M+).

後処理

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (150 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 100:0->0:100 gradient)

出典と根拠

ORDレコード
ord-5a85f045d899436aa578f818f151588d
出典データセット
uspto-grants-2009_05
特許番号
US07531529B2

関連ノート

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