Diethyl Ether → Ethyl 4-methyl-1h-pyrrole-3-carboxylate

HRID 1359675Notes

Reaction equation

HRID 1359675 reaction equation
[H-].[Na+].[C:3]([O:8][CH2:9][CH3:10])(=[O:7])/[CH:4]=[CH:5]/[CH3:6].CC1C=CC(S([CH2:21][N:22]=C)(=O)=O)=CC=1.[CH2:24](OCC)C>CS(C)=O>[CH2:9]([O:8][C:3]([C:4]1[C:5]([CH3:24])=[CH:6][NH:22][CH:21]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 429065Ethyl trans-crotonateHCID 562852HCID 562852, compound

Product 1

HCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (4 g of 60% dispersion, 2eq, washed with diethyl ether) in diethyl ether (200 mL), cooled in an ice bath with stirring was added slowly a solution of ethyl crotonate (6.2 mL, 50 mmol) and p-tosylmethyl isocyanide (9.7 g, 50 mmol) in 80 mL of DMSO and 160 mL diethyl ether. Upon complete addition of the solution, the reaction mixture was stirred at room temperature for 1 hr. The reaction was quenched with 400 mL water and extracted into diethyl ether (2×100 mL), dried (MgSO4) and concentrated to afford 6 g (78%) of 4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester as a brown oil which solidified upon standing.

Workup

  1. temperaturecooled in an ice bath
  2. additionUpon complete addition of the solution
  3. stirringthe reaction mixture was stirred at room temperature for 1 hr
  4. customThe reaction was quenched with 400 mL water
  5. extractionextracted into diethyl ether (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-483147e38ef1419586f6e5660fd26119
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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