Methyl 7-phthalimidohept-5-ynoate → Methyl (Z)-7-phthalimidohept-5-enoate

HRID 358622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358622
[C:1]1(=[O:21])[N:5]([CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[C:4]1(=[O:16])[N:5]([CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:1](=[O:21])[C:2]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:3]12

Komponenten

4

Edukt 1

HCID 20066955Methyl 7-phthalimidohept-5-ynoate

Produkt 1

HCID 86744641Methyl (Z)-7-phthalimidohept-5-enoateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 7-phthalimidohept-5-ynoate (1.9 g) and Lindlar catalyst (250 mg) in methanol (130 ml) was shaken under an atmosphere of hydrogen at 30 psi for 2.5 hours. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel eluted with chloroform to give the title compound (1.59 g) as a low melting solid. m.p. 47°-49° C.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was chromatographed on silica gel
  4. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-24b73d17d1734779bbe7d9e1dc63965f
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997847

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