1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne → 1-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropene

HRID 464932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464932
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1>O1CCCC1.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1

Komponenten

4

Edukt 1

HCID 128782521-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne

Produkt 1

HCID 539580771-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2.0 g (5 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropyne and 0.1 g of prehydrogenated 10% palladium on barium sulfate in 50 ml of tetrahydrofuran was hydrogenated at room temperature and atmospheric pressure until 85 ml of hydrogen was absorbed. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to dryness. The residue was crystallized from ether to give a white solid, mp 70°-72° C. Recrystallization from ether gave colorless prisms, mp 70°-72° C.

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. customatmospheric pressure until 85 ml of hydrogen was absorbed
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated at reduced pressure to dryness
  5. customThe residue was crystallized from ether
  6. customto give a white solid, mp 70°-72° C
  7. customRecrystallization from ether
  8. customgave colorless prisms, mp 70°-72° C.

Quellen und Nachweise

ORD-Eintrag
ord-c0b48c2361d1411fadcd11f98d924cc4
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04549988

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