Water → 2-Benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole

HRID 1090851Notes

Reaction equation

HRID 1090851 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].I[CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[C:22]([C:18]1[N:17]([CH2:16][CH2:15][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:21]=[CH:20][CH:19]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 14975129[1-(2-Iodoethyl)-1H-pyrrol-2-yl](phenyl)methanone

Product 1

HCID 149751302-Benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrroleYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of diethyl malonate (5.40 g, 33.8 mmol) in anhydrous N,N-dimethylformamide (50 mL) at 0° C. was added sodium hydride (60% in mineral oil, 1.35 g, 33.8 mmol). The reaction mixture was warmed and stirred at room temperature for 30 minutes. To this mixture was then added a solution of 1-(2-iodoethyl)-2-benzoylpyrrole (11.0 g, 33.8 mmol) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred at room temperature for 16 hours. The mixture was poured into water (1000 mL) and extracted with ethyl acetate (3×300 mL). The ethyl acetate extracts were combined, washed with water (2×200 mL) and saturated aqueous sodium chloride (300 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to provide 9.85 g (82%) of 2-benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole.

Workup

  1. temperatureThe reaction mixture was warmed
  2. stirringThe reaction mixture was stirred at room temperature for 16 hours
  3. extractionextracted with ethyl acetate (3×300 mL)
  4. washwashed with water (2×200 mL) and saturated aqueous sodium chloride (300 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-afd9d659dc3947bb99757f6b293ec2bc
Source dataset
uspto-grants-1992_01
Patent number
US05082951

Reaction notes

Loading…