Ethylene Glycol → 2-Hydroxyethyl 4-(4-chlorophenyl)pyrrole-2-carboxylate

HRID 1980949Notes

Reaction equation

HRID 1980949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:11][NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=O)=[CH:4][CH:3]=1.C(O)C[OH:21]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:13]([C:14]([O:16][CH2:17][CH2:18][OH:21])=[O:15])[NH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 731653222-(4-Chlorophenyl)-3-carbethoxymethylaminoacrylaldehyde

Product 1

HCID 130642732-Hydroxyethyl 4-(4-chlorophenyl)pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Chlorophenyl)-3-carbethoxymethylaminoacrylaldehyde (73.6 g.) was refluxed in 300 ml. of ethylene glycol for 10 minutes. The reaction mixture was cooled, diluted with 1 liter of water, product extracted into chloroform, treated with activated carbon and evaporated to solids. Trituration with ether gave crude product (8 g.). An additional quantity of crude product (7.5 g.) crystallized from the aqueous phase which had been standing. Recrystallization of the combined crude solids from chloroform gave 2-hydroxyethyl 4-(4-chlorophenyl)pyrrole-2-carboxylate (5 g., m.p. 128°-130° C.). The ether and chloroform mother liquors were combined and evaporated to yield an additional 40 g. of crude product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted into chloroform
  3. additiontreated with activated carbon
  4. customevaporated to solids
  5. customTrituration with ether gave crude product (8 g.)
  6. customAn additional quantity of crude product (7.5 g.) crystallized from the aqueous phase which
  7. customRecrystallization of the

Sources & evidence

ORD record
ord-43d5b98578ad482daf38a808ed7e8e00
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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