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

HRID 638312

反応式

HRID 638312 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-f27f10d9392e45628b59d516299f3422
出典データセット
uspto-grants-1985_12
特許番号
US04560699

関連ノート

読み込み中…