Sodium Chloride → Ethyl 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylate

HRID 2427406ノート

反応式

HRID 2427406 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH3:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])[CH3:4].[CH3:20]I.[Na+].[Cl-]>C1COCC1.O.C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:20])[CH:10]=[C:11]([CH3:19])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])[CH3:4]

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 107045911H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl ester

生成物 1

HCID 378982Ethyl 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylate収率 77%

試薬・触媒・溶媒 3

HCID 962Water触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (436 mg, 60% in mineral oil, 10.9 mmol) was added to a solution of 4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.25 g, 5.45 mmol) in THF (10 mL) at 0° C. and under nitrogen as inert gas and the reaction mixture was stirred for 15 min. Then methyl iodide (1,547 g, 10.9 mmol) was added to the reaction mixture and the reaction mixture was stirred for 1 h at 0° C. and overnight at RT. After the addition of a few drops of water and aq. sat. NaCl solution (250 mL), extraction was performed with DCM (2×250 mL). After drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification was performed by means of column chromatography. The desired product 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.02 g, 77% of theoretical) was obtained.

後処理

  1. stirringthe reaction mixture was stirred for 1 h at 0° C. and overnight at RT
  2. dry with materialAfter drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification

出典と根拠

ORDレコード
ord-3d9e80c908304864a84186d00d951c29
出典データセット
uspto-grants-2011_06
特許番号
US07968591B2

反応ノート

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