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

HRID 1981031노트

반응식

HRID 1981031 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c48e3784807549cdbae592f25e6b98b4
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04511576

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