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

HRID 1703308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1703308
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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 chloform, 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.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted into chloform
  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

Quellen und Nachweise

ORD-Eintrag
ord-60ec72b7ec164c2984bc8ea983da155e
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04351843

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