Water → 5-(Ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole-3-propanoic Acid Methyl Ester

HRID 24532

反応式

HRID 24532 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2].O.[N+]([O-])([O-])=[O:21].[NH4+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:18]=[O:21])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 22985Ammonium nitrateHCID 291754Ethyl 4-(3-methoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 516892Sodium Bicarbonate

生成物 1

HCID 155335575-(Ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole-3-propanoic Acid Methyl Ester収率 60%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3,5-Dimethyl-4-(2-methoxycarbonylethyl)-1H-pyrrole-2-carboxylic acid ethyl ester (127 g) was dissolved in acetic acid (1900 mL), water (1900 mL) and tetrahydrofuran (1900 mL) and cooled to −30° C. Cerric ammonium nitrate (1097 g) was added in portions with stirring to give a reddish-orange suspension. The suspension was stirred at 0° C. for 2 hours, neutralized to pH 7 with sodium bicarbonate and extracted with ethyl acetate (2000 mL). The ethyl acetate layer was separated, washed with brine (200 mL) and dried over anhydrous sodium sulfate (20 g). The solvent was removed to give 80.2 g (60%) of 5-formyl-4-(2-methoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as an oil.

後処理

  1. customto give a reddish-orange suspension
  2. stirringThe suspension was stirred at 0° C. for 2 hours
  3. extractionextracted with ethyl acetate (2000 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine (200 mL)
  6. dry with materialdried over anhydrous sodium sulfate (20 g)
  7. customThe solvent was removed

出典と根拠

ORDレコード
ord-426649ba0d404dc2b8a941cfef53a11d
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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