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

HRID 358622Notes

Reaction equation

HRID 358622 reaction equation
[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

Participants

4

Reactant 1

HCID 20066955Methyl 7-phthalimidohept-5-ynoate

Product 1

HCID 86744641Methyl (Z)-7-phthalimidohept-5-enoateYield 83.1%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-24b73d17d1734779bbe7d9e1dc63965f
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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