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

HRID 1090816

Reaction equation

HRID 1090816 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-33ebbc89a0c548bb9ffa19accf250378
Source dataset
uspto-grants-1992_01
Patent number
US05082950

Linked notes

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