2-Nitro-1-phenylpropene → 1H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl ester

HRID 880416ノート

反応式

HRID 880416 の反応式
N12CCCN=C1CCCCC2.[N+:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[C-:13].[N+]([C:23](=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:24])([O-])=O>O1CCCC1.C(O)(C)C>[CH3:24][C:23]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:12][CH:13]=1

参加物

6

反応物 3

HCID 128072-Nitro-1-phenylpropeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetate

生成物 1

HCID 107045911H-Pyrrole-2-carboxylic acid, 4-methyl-3-phenyl-, ethyl ester収率 90%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1,8-Diazabicyclo[5.4.0]undec-7-ene (3.70 g, 24.6 mmol) was added dropwise to a stirred solution of ethyl isocyanoacetate (1.50 g, 13.3 mmol) and 2-nitro-3-phenyl-2-propene (2.0 g, 12.3 mmol) in a mixture of tetrahydrofuran (15 mL) and iso-propanol (5 mL) at between 10 and 20° C. The reaction mixture was stirred at room temperature for 4 h. Excess tetrahydrofuran was removed in vacuo, water (15 mL) was added to the residue and the mixture was extracted with diethyl ether (3×25 mL). The combined organic phases were washed with brine (2×15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford ethyl 4-methyl-3-phenyl-1H-pyrrole-2-carboxylate (2.5 g, 90%) as an oil.

後処理

  1. customExcess tetrahydrofuran was removed in vacuo, water (15 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with diethyl ether (3×25 mL)
  4. washThe combined organic phases were washed with brine (2×15 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-04426b214d40433889e50de2a6e1a759
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

反応ノート

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