Diethyl Malonate → Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate

HRID 1090814

反応式

HRID 1090814 の反応式
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>C(O)(=O)C.C(OCC)C.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[C:1]([C:9]1[NH:10][C:11]([CH2:26][C:25]([O:28][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])=[O:27])=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 7761Diethyl MalonateHCID 24370Phenyl(1H-pyrrol-2-YL)methanoneHCID 517045Sodium Acetate

生成物 1

HCID 57231278Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate収率 57%

試薬・触媒・溶媒 3

HCID 12416832Manganese triacetate dihydrate触媒HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-benzoylpyrrole (855 mg, 5 mmol), diethyl malonate (800 mg, 5 mmol), manganese(III) acetate dihydrate (4560 mg, 15 mmol) and sodium acetate (820 mg, 10 mmol) in acetic acid (30 mL) was stirred at 70° C. under a nitrogen atmosphere. The reaction mixture was diluted with diethyl ether and filtered. The filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (70:30) to provide 1.00 g (57%) of diethyl (5-benzoylpyrrol-2-yl)acetoxy-methanedicarboxylate.

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (70:30)

出典と根拠

ORDレコード
ord-5c72ba68032442c5a009dccd10bf06b8
出典データセット
uspto-grants-1992_01
特許番号
US05082950

関連ノート

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