Chlorosuccinimide → Ethyl 4-chloro-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

HRID 554219ノート

反応式

HRID 554219 の反応式
[CH3:1][C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:18]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:18][C:5]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[NH:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 12258777Ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

生成物 1

HCID 12808304Ethyl 4-chloro-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate収率 44.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution (20 mL) of ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate (1.0 g) in N,N-dimethylformamide was added N-chlorosuccinimide (874 mg) at 0° C. The reaction mixture was stirred at room temperature for 4 hr, 6% aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as colorless crystals (yield 509 mg, 44%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

出典と根拠

ORDレコード
ord-8ae35762928e4c3dbc0d5c2cdd80c8af
出典データセット
uspto-grants-2011_11
特許番号
US08048909B2

反応ノート

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