4-Ethynylbenzoic acid → methyl 5-(4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

HRID 638313

Reaction equation

HRID 638313 reaction equation
[CH:1]1([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][N:3]2[CH:6]=[CH:7][CH:8]=[C:2]12.[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1)#[CH:14]>C1(C)C(C)=CC=CC=1>[C: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]([O:11][CH3:12])=[O:10])[C:2]3=[CH:8][CH:7]=2)=[O:20])=[CH:17][CH:16]=1)#[CH:14]

Participants

4

Reactant 2

HCID 5897064-Ethynylbenzoic acidHCID 12795075Methyl 2,3-dihydro-1H-pyrrolizine-1-carboxylate

Product 1

HCID 13487007methyl 5-(4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate (2.50 g, 0.015 mole) in dry xylene (100 ml) containing the acid chloride of 4-ethynylbenzoic acid [4.40 g, 0.026 mole; L. E. Salisbury, J. Org. Chem., 43, 4987 (1978)] was heated at reflux temperature for 12 hours. The solvent was removed in vacuo and the residue was purified by chromatography on alumina (200 g) using hexane/ethyl acetate (95:5) as the eluting solvent to give methyl 5-(4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate, m.p. 113°-114° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 12 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography on alumina (200 g)

Sources & evidence

ORD record
ord-5eb8a850a61a44ad98289270ebab81fa
Source dataset
uspto-grants-1985_12
Patent number
US04560699

Linked notes

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