4-Vinylbenzoic acid → 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid

HRID 638312

반응식

HRID 638312 반응식
[CH:1]1([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4][N:3]2[CH:6]=[CH:7][CH:8]=[C:2]12.[CH:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1)=[CH2:14]>C1(C)C(C)=CC=CC=1>[CH:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([C:6]2[N:3]3[CH2:4][CH2:5][CH:1]([C:9]([OH:11])=[O:10])[C:2]3=[CH:8][CH:7]=2)=[O:20])=[CH:17][CH:16]=1)=[CH2:14]

참가 물질

4

반응물 2

HCID 140984-Vinylbenzoic acidHCID 12795075Methyl 2,3-dihydro-1H-pyrrolizine-1-carboxylate

생성물 1

HCID 134870625-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid수율 36%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A solution of methyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (Formula B where Y is hydrogen) the synthesis of which is described in Preparations 1 and 2 hereinabove, (3.0 g, 18 mmol) and the acid chloride of 4-vinylbenzoic acid [J. Chem. Education, 55, 813 (1978)] (10.0 g, 60 mmol) in anhydrous xylene (100 ml) was heated at reflux temperature for 6 hours. The solvent was removed in vacuo and the residue was purified by column chromatography on Act II neutral alumina (Fluka, 200 g). The product was eluted with hexane-ethyl acetate (95:5) to give 5-(4-vinylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2,a]pyrrole-1-carboxylic acid, (36%) which had mp 99°-100° after crystallization from methanol. The purified product exhibited the following characteristics:

후처리

  1. temperatureat reflux temperature for 6 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on Act II neutral alumina (Fluka, 200 g)
  4. washThe product was eluted with hexane-ethyl acetate (95:5)

출처 및 근거

ORD 기록
ord-f27f10d9392e45628b59d516299f3422
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560699

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