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

HRID 638312

Reaction equation

HRID 638312 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-f27f10d9392e45628b59d516299f3422
Source dataset
uspto-grants-1985_12
Patent number
US04560699

Linked notes

Loading…