1,2-Dichloroethane → 77640-10-9

HRID 127599Notes

Reaction equation

HRID 127599 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[Cl-].[Al+3].[Cl-].[Cl-].C([CH:13]([C:17](Cl)=[O:18])[C:14](Cl)=[O:15])C.[OH2:20].Cl[CH2:22][CH2:23]Cl>ClC(Cl)C>[CH2:22]([O:20][C:17](=[O:18])[CH2:13][C:14](=[O:15])[C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)[CH3:23]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 73041-MethylpyrroleHCID 6451240Aluminum(III) ChlorideHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 1035262977640-10-9

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The starting material is prepared as follows: To the solution of 17 g of 1-methylpyrrole in 400 ml of 1,2-dichloroethane is added 28 g of anhydrous aluminum chloride in portions, while stirring and cooling to 10°-15°, followed by 27 g of ethyl malonyl chloride in 50 ml of dichloroethane at such a rate to keep the temperature between 10° and 15°. After stirring for 3.5 hours the temperature is allowed to rise slowly to 32° and the mixture is allowed to stand overnight at room temperature. It is treated with water, shaken, the organic layer separated, washed twice with water, dried and evaporated. The residual dark brown oil is distilled and the fraction boiling at 105-112/0.25 mm Hg collected, to yield the 1-methyl-β-oxo-2-pyrrolpropionic acid ethyl ester.

Workup

  1. customThe starting material is prepared
  2. temperaturecooling to 10°-15°
  3. customthe temperature between 10° and 15°
  4. stirringAfter stirring for 3.5 hours the temperature
  5. customto rise slowly to 32°
  6. stirringshaken
  7. customthe organic layer separated
  8. washwashed twice with water
  9. customdried
  10. customevaporated
  11. distillationThe residual dark brown oil is distilled
  12. customcollected

Sources & evidence

ORD record
ord-626e48f60a28482aa9b84ffb09a64300
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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