Methyl iodide → methyl 5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1518714ノート

反応式

HRID 1518714 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:10]([CH3:12])[CH:11]=1)=[O:6].[CH3:20]I>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH3:20])[C:9]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:10]([CH3:12])[CH:11]=1)=[O:6]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68286466methyl 5-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 68286033methyl 5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate収率 81.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred solution of sodium hydride (60% suspension in mineral oil) (0.529 g, 13.22 mmol) in DMF (5 ml) at 0° C. was added a solution of methyl-5-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (prepared according to the procedure reported in J. org. Chem., 2009, 74(2), 903-905, Org. Lett. 2007, 9(25), 5191-5194, 2.20 g, 8.81 mmol) in DMF (10 ml), which was then followed by the addition of methyl iodide (1.88 g, 0.83 ml, 13.22 mmol). The resulting reaction mixture was stirred at room temperature for 45 minutes. The progress of the reaction was monitored by TLC. The reaction mixture was then quenched with water (10 ml). The mixture so obtained was then extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 15-20% ethyl acetate in hexanes as an eluent to obtain the title compound (1.9 g, 81.9%)

後処理

  1. customprepared
  2. customThe resulting reaction mixture
  3. customThe reaction mixture was then quenched with water (10 ml)
  4. customThe mixture so obtained
  5. extractionwas then extracted with ethyl acetate (2×50 ml)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customThe solvent was evaporated from the dried organic layer under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-e841f23e5e66430eb798a20408f5f1d2
出典データセット
uspto-grants-2015_07
特許番号
US09072731B2

反応ノート

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