Succinic anhydride → 5-(Ethoxycarbonyl)-gamma-oxo-1H-pyrrole-3-butanoic acid

HRID 1843201Notes

Reaction equation

HRID 1843201 reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].[Al+3].[Cl-].[Cl-].[Cl-].[NH:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>ClCCCl>[CH2:20]([O:19][C:17]([C:13]1[NH:12][CH:16]=[C:15]([C:2](=[O:7])[CH2:3][CH2:4][C:5]([OH:1])=[O:6])[CH:14]=1)=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 239083965-(Ethoxycarbonyl)-gamma-oxo-1H-pyrrole-3-butanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Into a 3000-mL 4-necked round-bottom flask was placed a solution of oxolane-2,5-dione (100 g, 999.27 mmol, 2.00 equiv) in 1,2-dichloroethane (690 mL) and AlCl3 (400.5 g, 3.00 mol, 6.00 equiv), followed by the addition of a solution of ethyl 1H-pyrrole-2-carboxylate (69 g, 495.86 mmol, 1.00 equiv) in 1,2-dichloroethane (660 mL) dropwise with stirring at room temperature over 20 min (FIG. 14). The resulting solution was stirred at room temperature for 3 h and quenched by the addition of 3 kg of water/ice. The solids were collected by filtration, washed with 1×1000 mL of water and dried in a vacuum oven to afford 105 g (89%) of 113g as a white solid.

Workup

  1. customInto a 3000-mL 4-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred at room temperature for 3 h
  3. customquenched by the addition of 3 kg of water/ice
  4. filtrationThe solids were collected by filtration
  5. washwashed with 1×1000 mL of water
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-62f7ff6500b44b4ebadab6b47090c4de
Source dataset
uspto-grants-2015_02
Patent number
US08946213B2

Reaction notes

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