methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate → Methyl 4-[2-(4-pyridyl)ethyl]benzoate

HRID 636517Notes

Reaction equation

HRID 636517 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]\[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1>CO.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 70244616methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate

Product 1

HCID 21254785Methyl 4-[2-(4-pyridyl)ethyl]benzoateYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate (570 mg) in methanol (5.7 ml) was added 10% palladium on carbon, and the mixture was stirred for 4 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was crystallized with n-hexane to give methyl 4-[2-(4-pyridyl)ethyl]benzoate (539 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was crystallized with n-hexane

Sources & evidence

ORD record
ord-70ade6e382b746f3bc0f8ec337b75590
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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