Trichloroacetyl chloride → 2-(2-Trichloroacetylpyrrol-1-yl)malonic acid diethyl ester

HRID 256586

Reaction equation

HRID 256586 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl:17][C:18]([Cl:23])([Cl:22])[C:19](Cl)=[O:20]>C(Cl)(Cl)Cl>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([N:11]1[CH:12]=[CH:13][CH:14]=[C:15]1[C:19](=[O:20])[C:18]([Cl:23])([Cl:22])[Cl:17])[C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH3:10]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 2782128diethyl 2-(1H-pyrrol-1-yl)malonate

Product 1

HCID 105471632-(2-Trichloroacetylpyrrol-1-yl)malonic acid diethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(pyrrol-1-yl)malonic acid diethyl ester (100.0 g) in chloroform (100 ml) was added trichloroacetyl chloride (161.4 g), and the resulting mixture was refluxed for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with 10% aqueous sodium carbonate solution and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from isopropyl ether to give the title compound (146.4 g, 89.0%) as colorless crystals, mp 67°-69° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 15 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with 10% aqueous sodium carbonate solution
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-fb9e6de47aa948b9b0384c1ba25e19a7
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Linked notes

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