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

HRID 256587

Reaction equation

HRID 256587 reaction equation
[CH:1]1([CH3:24])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([O:10][C:11](=[O:23])[CH:12]([N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1.[Cl:25][C:26]([Cl:31])([Cl:30])[C:27](Cl)=[O:28]>C(Cl)(Cl)Cl>[CH:1]1([CH3:24])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:8])[CH3:9])[CH:3]([O:10][C:11](=[O:23])[CH:12]([N:18]2[CH:19]=[CH:20][CH:21]=[C:22]2[C:27](=[O:28])[C:26]([Cl:31])([Cl:30])[Cl:25])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 538719252-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester

Product 1

HCID 536822462-(2-Trichloroacetylpyrrol-1-yl)malonic acid ethyl (-)-menthyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester (64.0 g) in chloroform (80 ml) was added trichloroacetyl chloride (69.0 g), and the resulting mixture was refluxed for 7 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with 5% aqueous sodium carbonate solution and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (50:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure to give the title compound (87.0 g, 94.9%) as a colorless oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 7 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with 5% aqueous sodium carbonate solution
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. additionFractions containing the title compound
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-092fc3f815bd4e3e90d5e158a41ec604
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Linked notes

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