Pyrrole → HCID 19994527, compound

HRID 2248590Notes

Reaction equation

HRID 2248590 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[H][H].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]I)[CH3:11]>CN(C)C=O.O>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][N:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1)[CH3:11]

Participants

7

Reactant 4

HCID 8027PyrroleHCID 24758Sodium hydrideHCID 125047911,1-Diethoxy-2-iodoethaneHCID 178418361HCID 178418361, compound

Product 1

HCID 19994527HCID 19994527, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a cold solution (-5° C. to 0° C.) of sodium hydride in anhydrous dimethylformamide (11.8 g, 245.9 mmol), pyrrole (15.0 g, 223.6 mmol) in dry dimethylformamide was slowly added while stirring vigorously. The reaction was completed, and the temperature raised to room temperature. After hydrogen is fully evolved, iodoacetaldehyde diethyl acetal was added (65.5 g, 268.1 mmol) to the reaction mixture. The reaction mixture was allowed to reflux for 5 hours or until there was no further advance of the reaction. The reaction mixture was cooled to room temperature, poured onto 50 mL of water, extracted with ether, dried over MgSO4, and concentrated. The product was purified by column chromatography [silica gel, hexane] to give the title compound, 1-(2,2-diethoxyethyl)pyrrole, (95%), ms 183 (M+).

Workup

  1. temperatureto reflux for 5 hours or until there
  2. customno further advance of the reaction
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with ether
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography [silica gel, hexane]

Sources & evidence

ORD record
ord-f104a1680f5e4dbaa272cc4614e9465c
Source dataset
uspto-grants-1991_08
Patent number
US05041442

Reaction notes

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