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

HRID 638313

Reaktionsgleichung

Reaktionsgleichung von HRID 638313
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5eb8a850a61a44ad98289270ebab81fa
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560699

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