Benzene → N-(Ethylcarboethoxy)pyrrole

HRID 1576275Notes

Reaction equation

HRID 1576275 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[K].C(C(Cl)(C)[C:10]([O-:12])=[O:11])C.O.[CH:16]1C=C[CH:19]=[CH:18][CH:17]=1>>[CH2:17]([CH2:18][CH2:19][O:12][C:10]([N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[O:11])[CH3:16]

Participants

5

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 19993353EthylchloropropionateHCID 241923201H-Pyrrole, potassium salt (1:1)

Product 1

HCID 22468057N-(Ethylcarboethoxy)pyrrole

Conditions

Temperature
80 °C

Procedure

After adding 30 ml of benzene to the potassium pyrrole, a solution of 30.0 g (0.22 mole) of ethylchloropropionate in 30 ml benzene is slowly added to the paste over a period of 1 hour with constant stirring. The reaction mixture is heated to 80°C for 30 minutes. Then 100 ml of water is added and the mixture is extracted with diethyl ether. The ether extract is dried over anhydrous magnesium sulfate and the dried extract is evaporated to yield residue which is distilled under vacuum. The pyrrole derivative having the formula given above is obtained as 3 g of a colorless liquid with a boiling point of 108°C at 14 mm Hg pressure. MS shows the m/e peaks: 80, 94, 167, 27, 95.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. extractionThe ether extract
  3. dry with materialis dried over anhydrous magnesium sulfate
  4. extractionthe dried extract
  5. customis evaporated
  6. customto yield residue which
  7. distillationis distilled under vacuum

Sources & evidence

ORD record
ord-a4d36eedf32440ccaf90c49420657ff3
Source dataset
uspto-grants-1976_09
Patent number
US03980089

Reaction notes

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