Methyl iodide → Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

HRID 515864

反応式

HRID 515864 の反応式
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12]I.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][N:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]1[CH3:1]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

生成物 1

HCID 12211514Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 10 g of ethyl 2-methyl-1H-pyrrole-3-carboxylate (65.3 mmol) and 8.95 mL (130.6 mmol) of methyl iodide in 70 mL of dimethylformamide placed at 0° C. there are added, in three portions, 2.61 g (65.3 mmol) of sodium hydride (NaH) 60% . The batch is then stirred at 0° C. for 1 hour. Then, the reaction mixture is hydrolysed by the addition of 420 mL of ice-cold water. The reaction mixture is then diluted with ethyl acetate, successively washed with 0.1M aqueous hydrochloric acid (HCl) solution, saturated aqueous LiCl solution and then brine. The organic phase is then dried over MgSO4, filtered, concentrated to dryness and purified by chromatography over silica gel (petroleum ether/AcOEt gradient).

後処理

  1. customplaced at 0° C.
  2. washsuccessively washed with 0.1M aqueous hydrochloric acid (HCl) solution, saturated aqueous LiCl solution
  3. dry with materialThe organic phase is then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. custompurified by chromatography over silica gel (petroleum ether/AcOEt gradient)

出典と根拠

ORDレコード
ord-527b8670a95e40e989aab6cfe6fb9720
出典データセット
uspto-grants-2015_08
特許番号
US09108983B2

関連ノート

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