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

HRID 1090816

Reaktionsgleichung

Reaktionsgleichung von HRID 1090816
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 9949366Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylateAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-33ebbc89a0c548bb9ffa19accf250378
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082950

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