Water → Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate

HRID 1090816

反応式

HRID 1090816 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.Br[CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(B(CC)CC)C.O>C1C=CC=CC=1>[C:1]([C:9]1[NH:10][C:11]([CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 7357Triethylborane2 回HCID 24370Phenyl(1H-pyrrol-2-YL)methanoneHCID 69637Diethyl bromomalonate

生成物 1

HCID 9949366Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate収率 86.2%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of 2-benzoylpyrrole (171mg, 1 mmol) and diethyl bromomalonate (1185 mg, 5 mmol) in benzene (20 mL) was added triethylborane (1.0 M in hexane, 5 mL, 5 mmol). The reaction mixture was stirred for 1 hour in an open vessel. Additional triethylborane (1 mL, 1 mmol) was added and the reaction was stirred for an additional hour. The mixture was poured into water and extracted with diethyl ether. The ethereal extract was washed with saturated aqueous sodium chloride, dried (Na2SO4), and concentrated. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13) to provide 284 mg (86%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.

後処理

  1. stirringthe reaction was stirred for an additional hour
  2. extractionextracted with diethyl ether
  3. extractionThe ethereal extract
  4. washwas washed with saturated aqueous sodium chloride
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13)

出典と根拠

ORDレコード
ord-33ebbc89a0c548bb9ffa19accf250378
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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